One-pot method to synthesize 4,6-bis(isopropylamino)resorcinol through hydrodechlorination and catalytically reductive mono-N-alkylation

Zhonghao Jin; Dao Li; Rui Ma; Xutao Peng; Xingyi Wang; Guanzhong Lu

Journal of Industrial and Engineering Chemistry, Vol.15, No.3, 434-437, May, 2009

DOI10.1016/j.jiec.2008.11.004 Export Citation

One-pot method to synthesize 4,6-bis(isopropylamino)resorcinol through hydrodechlorination and catalytically reductive mono-N-alkylation

Zhonghao Jin, Dao Li, Rui Ma, Xutao Peng, Xingyi Wang^†, and Guanzhong Lu

Laboratory for Advanced Materials, Research Institute of Industrial Catalysis, East China University of Science and Technology, Shanghai 200237, China

E-mail:

2-Chloro-4,6-dinitroresorcinol was converted catalytically in one-pot operation to the corresponding Nalkyl secondary aminophenol, 4,6-bis(isopropylamino)resorcinol, in high yield by using acetone as alkyl source and hydrogen as reducing reagent over 10 wt.% Pd/C catalyst. The effects of reaction conditions, such as the amount of acetic acid, concentration of acetone, catalyst amount, and reaction time on the selectivity of 4,6-bis(isopropylamino)resorcinol were investigated.

Keywords:One-pot reductive mono-N-alkylation;Hydrodechlorination;2-Chloro-4,6-dinitroresorcinol;4,6-Bis(isopropylamino)resorcinol

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[1] Kalgutkar AS, Kozak KR, Crews BC, Hochgesang GP, Marnett LJ, J. Med. Chem., 41, 4800 (1998)

[2] Clark RF, Zhang T, Xin Z, Liu G, Wang Y, Hansen TM, Wang X, Frevert EU, Camp HS, Beutel BA, Sham HL, Gu YG, Bioorg. Med. Chem. Lett., 16, 6078 (2006)

[3] Combs DC, Rampulla MS, Bell SC, Klaubert DH, Tobia AJ, Falotico R, Haerthein B, Kakas-Weiss C, Moore JBL, Med. Chem., 33, 380 (1990)

[4] Byun E, Hong B, De Castro KA, Lim M, Rhee H, J. Org. Chem., 72, 9815 (2007)

[5] Ju HY, Manju MD, Kim KH, Park SW, Park DW, J. Ind. Eng. Chem., 14(2), 157 (2008)

[6] Sydnes MO, Isobe M, Tetrahedron Lett., 49, 1199 (2008)

[7] Zhou XJ, Wu ZW, Li L, Wang GJ, Li JP, Dyes Pigments, 36, 365 (1998)

[8] Kim SH, Oh SS, Kim SH, Kim GJ, J. Ind. Eng. Chem., 11(4), 522 (2005)

[9] Fache F, Valot F, Milenkovic A, Lemaire M, Tetrahedron, 52, 9777 (1996)

[10] Freedman HH, Frost AE, J. Org. Chem., 23, 1292 (1958)

[11] Yang S, Lai H, Tsai Y, Tetrahedron Lett., 45, 2693 (2004)

[12] Chen XQ, Sun Q, Huang YD, Huaxue. Shiji., 27, 681 (2005)

[13] Mcgrath PJ, WO 9319035 (1993)

[14] Liu MB, Kleiss LR, WO 9101967 (1991)

[15] Zenon L, EP 266222 (1988)

[16] Zenon L, US 4,766,244 (1988)

[17] Bodalski R, Quin LD, J. Org. Chem., 56, 2666 (1991)

[18] Kratky V, Kralik M, Mecarova M, Stolcova M, Zalibera L, Hronec M, Appl. Catal. A: Gen., 235(1-2), 225 (2002)

[19] Lassova L, Lee HK, Andy Hor TS, J. Mol. Catal. A, 144, 397 (1999)

[20] Nader BS, US 5,371,291 (1994)

[21] Bouchenafa-Saib N, Grange P, Verhasselt P, Addoun F, Dubois V, Appl. Catal. A: Gen., 286(2), 167 (2005)