2-Chloroaniline → HCID 60046939, compound

HRID 1672332Notes

Reaction equation

HRID 1672332 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[Cl:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20]>C(O)(=O)C>[Cl:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH:20][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 72402-ChloroanilineHCID 60046942HCID 60046942, compound

Product 1

HCID 60046939HCID 60046939, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound is prepared in analogy to Example 19d starting from 0.7 g (2.957 mmol) of 4-chloro-6-ethyl-3-nitro-quinoline (Example 49e) and 0.37 g (3.55 mmol) 2-chloroaniline in 3 ml acetic acid. Crystallization from ethyl acetate-hexane. mp: 134-136° C.; MS: 328 (M++1); HPLC: tret=10.61 min (Grad 1).

Workup

  1. customCrystallization from ethyl acetate-hexane
  2. customtret=10.61 min (Grad 1)

Sources & evidence

ORD record
ord-b7e7f968a76f4771806e58d9b2f4bf89
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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