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

HRID 1447311Notes

Reaction equation

HRID 1447311 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-27b135a383de4ce99b8591d7250734fa
Source dataset
uspto-grants-1982_02
Patent number
US04316847

Reaction notes

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