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

HRID 616264

Reaction equation

HRID 616264 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 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. additionbattery jar was charged
  2. customto give
  3. additiona highly viscous suspension of an orange precipitate
  4. stirringthe mixture stirred vigorously for 30 minutes
  5. filtrationThe product was collected by filtration
  6. washwashed with 1
  7. dry with material0 l of the same solvent mixture and dried at room temperature

Sources & evidence

ORD record
ord-f7b508a4a85e4e0e81dadd7d423e3276
Source dataset
uspto-grants-1978_02
Patent number
US04073795

Linked notes

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