Acetic Anhydride → HCID 22310834, compound

HRID 2305587Notes

Reaction equation

HRID 2305587 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH2:15])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:16]([O:18][CH3:19])=[O:17].[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[C:24]([NH:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:6]([CH2:5][C:4]1[CH:20]=[CH:21][C:22]([Cl:23])=[C:2]([Cl:1])[CH:3]=1)[C:7]([C:16]([O:18][CH3:19])=[O:17])=[CH:8]2)(=[O:26])[CH3:25]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 22310882HCID 22310882, compound

Product 1

HCID 22310834HCID 22310834, compoundYield 32%

Conditions

Temperature
90 °C

Procedure

Methyl N-(3,4-dichlorobenzyl)-5-aminoindole-2-carboxylate (0.28 g) was dissolved in acetic anhydride and heated to 90° C. for 1 hour. Upon cooling, the title compound crystallised as white needles, was filtered off, washed with diethyl ether and dried in vacuo to yield the desired end product (0.1 g, 32%); NMR δ(CD3SOCD3) 2.03 (s, 3H), 3.80 (s, 3H), 5.80 (s, 2H), 6.88 (m, 1H), 7.36 (m, 3H), 7.52 (d, 2H), 8.08 (s, 1H), 9.88 (s, 1H); M/z (−) 391 (M+), 389.

Workup

  1. temperatureUpon cooling
  2. customthe title compound crystallised as white needles
  3. filtrationwas filtered off
  4. washwashed with diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-761918151a154262915198bddf45ab8b
Source dataset
uspto-grants-2002_08
Patent number
US06441004B1

Reaction notes

Loading…