HCID 19367665, compound → HCID 19367647, compound

HRID 1459038Notes

Reaction equation

HRID 1459038 reaction equation
[CH3:1][C:2]1[C:10]2[S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:9]=2[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]([O:20]CC)=[O:19])[NH:6]2>CO.O>[CH3:1][C:2]1[C:10]2[S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:9]=2[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]([OH:20])=[O:19])[NH:6]2

Participants

4

Reactant 1

HCID 19367665HCID 19367665, compound

Product 1

HCID 19367647HCID 19367647, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 4-methyl-1H-[1]benzothieno[2,3-f]indole-2-carboxylate (1.0 g, 3.2 mmol) was suspended in a mixture of methanol (110 ml) and water (30 ml). Casium carbonate (10 g) was added and the mixture was heated at reflux under nitrogen for 2 h. The solution was allowed to cool to room temperature, and the methanol was removed in vacuo. The solution was acidified with 0.1 Molar Hydrochloric acid and the resulting yellow precipitate was collected by fitration and washed with water. The wet precipitate was dissolved in acetone and the solvent removed in vacuo to give the product as a yellow solid with m.p. 271°-272° C.; δH [2H6 ]-DMSO 11.88 (1H, s, 1-NH), 8.29 (1H, dd, J 6, 3, 9H), 8.18 (1H, s, 10-H), 7.89-7.99 (1H, m, 6-H), 7.44-7.54 (2H, m, 7-H, 8-H), 7.35 (1H, d, J 2, 3-H), 2.72 (3H, s, 4-CH3); m/z (%) 281 (90, M+), 263 (100), 235 (69).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under nitrogen for 2 h
  3. customthe methanol was removed in vacuo
  4. customthe resulting yellow precipitate was collected by fitration
  5. washwashed with water
  6. dissolutionThe wet precipitate was dissolved in acetone
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b0dda742183d43f9b89f79e49920e34d
Source dataset
uspto-grants-1998_12
Patent number
US05852204

Reaction notes

Loading…