Acetic Anhydride → Alphanitro-6-chloro-3-indoleacrylic acid methylester

HRID 1390840

반응식

HRID 1390840 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:11][O:12][C:13](=[O:22])[C:14]([N+:19]([O-:21])=[O:20])=[CH:15]OCC.C(OC(=O)C)(=O)C>>[CH3:11][O:12][C:13](=[O:22])[C:14]([N+:19]([O-:21])=[O:20])=[CH:15][C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1

참가 물질

4

반응물 3

HCID 7918Acetic AnhydrideHCID 871116-ChloroindoleHCID 53395203alpha-Nitro-beta-ethoxyacrylic acid methylester

생성물 1

HCID 53746644Alphanitro-6-chloro-3-indoleacrylic acid methylester수율 51%

실험 절차

A 4-l. battery jar was charged with 641 g (4.23 moles) of 6-chloroindole, 926 g (5.3 moles) of crude (ca. 85% pure) alpha-nitro-beta-ethoxy acrylic acid methylester and 475 g (4.65 moles) of acetic anhydride. The mixture was well stirred at room temperature for 45 hours to give a highly viscous suspension of an orange precipitate. 1.5 l of a mixture of benzene-ether-hexane 1:1:3 was added and the mixture stirred vigorously for 30 minutes. The product was collected by filtration, washed with 1.0 l of the same solvent mixture and dried at room temperature and 16 mmHg to constant weight to afford 600 g (51%) of product as orange crystals, m.p. 159-160°.

후처리

  1. customto give
  2. additiona highly viscous suspension of an orange precipitate
  3. stirringthe mixture stirred vigorously for 30 minutes
  4. filtrationThe product was collected by filtration
  5. washwashed with 1.0 l of the same solvent mixture
  6. customdried at room temperature

출처 및 근거

ORD 기록
ord-58b622ed50904ba6b4f829f14e777b58
출처 데이터셋
uspto-grants-1979_02
특허 번호
US04140697

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