Water → 2,5-Dibutoxy-4-chlorobenzenamine

HRID 375508Notes

Reaction equation

HRID 375508 reaction equation
[Cl-].[NH4+].O.[CH2:4]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][C:10]=1[N+:21]([O-])=O)[CH2:5][CH2:6][CH3:7]>C(O)(C)C>[CH2:4]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][C:10]=1[NH2:21])[CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 66635Benzene, 1,4-dibutoxy-2-chloro-5-nitro-

Product 1

HCID 144384592,5-Dibutoxy-4-chlorobenzenamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 84 parts of reduced iron, 8 parts of ammonium chloride, 35 parts of water and 160 parts of isopropanol was gradually added 60.3 parts of 2,5-dibutoxy-4-chloronitrobenzene under reflux to reduce the nitro compound. Post-treatment was carried out in a conventional manner to obtain 53 parts of 2,5-dibutoxy-4-chloroaniline (m.p.: 43° to 44° C.).

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-57fe3dbf7ebb4fe9bf09e3a2f9e2bfdd
Source dataset
uspto-grants-1996_01
Patent number
US05486446

Reaction notes

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