Water → HCID 60046937, compound

HRID 1672317Notes

Reaction equation

HRID 1672317 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C(O)(=O)C>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([N+:13]([O-:15])=[O:14])=[C:2]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 10681670Quinoline, 4,6-dichloro-3-nitro-

Product 1

HCID 60046937HCID 60046937, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.6 g (2.46 mmol) 4,6-dichloro-3-nitro-quinoline (Example 23c) and 0.247 ml (2.71 mmol) aniline in 4 ml acetic acid are stirred at rt for 4 h (tlc-control). A precipitate is formed. The reaction mixture is poured into 150 ml water. The solid is filtered off and washed with water and hexane. The filtrate is dissolved in ca. 50 ml diethylether, filtered from insoluble material, and the solvent is evaporated. The residue, yellow crystals, is dried at 60° C. over night. mp: 174-175° C. MS: 300 (M++1); HPLC: tret=10.53 min (Grad 1).

Workup

  1. customA precipitate is formed
  2. filtrationThe solid is filtered off
  3. washwashed with water and hexane
  4. dissolutionThe filtrate is dissolved in ca. 50 ml diethylether
  5. filtrationfiltered from insoluble material
  6. customthe solvent is evaporated
  7. customThe residue, yellow crystals, is dried at 60° C. over night
  8. customtret=10.53 min (Grad 1)

Sources & evidence

ORD record
ord-45d44d31b260439b9a40d5d6e93a3b66
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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