Aniline → 4-Anilino-3-nitrobenzoic acid

HRID 28668

反応式

HRID 28668 の反応式
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN1CCOCC1>COCCO>[NH:14]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 6115AnilineHCID 79724-MethylmorpholineHCID 679874-Fluoro-3-nitrobenzoic acid

生成物 1

HCID 38243664-Anilino-3-nitrobenzoic acid

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol溶媒

実験手順

4-Fluoro-3-nitrobenzoic acid (0.27 mol), an aniline (0.32 mol) and NMM (32.5 mL) in 2-methoxyethanol (750 mL) were stirred at reflux under argon for 24 h. The suspension was concentrated under reduced pressure and the residue was sonicated with 1M HCl (aq) over 1.5 h. The resultant orange solid was isolated by filtration, washed with water dried, then sonicated with t-butyl methyl ether, isolated by filtration and dried. Where necessary, the product was further purified by recrystallisation to yield the 4-anilino-3-nitrobenzoic acid: e.g. 4-(3-bromophenyl amino)-3-nitrobenzoic acid. (In some cases, for example with heteroaromatic anilines, NMN may be omitted from the reaction mixture).

後処理

  1. temperatureat reflux under argon for 24 h
  2. concentrationThe suspension was concentrated under reduced pressure
  3. customthe residue was sonicated with 1M HCl (aq) over 1.5 h
  4. customThe resultant orange solid was isolated by filtration
  5. washwashed with water
  6. customdried
  7. customsonicated with t-butyl methyl ether
  8. customisolated by filtration
  9. customdried
  10. customWhere necessary, the product was further purified by recrystallisation

出典と根拠

ORDレコード
ord-117d740f4ce941b198f1a4abcf68544e
出典データセット
uspto-grants-2008_09
特許番号
US07419995B2

関連ノート

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