Toluene → 3-(4-Dimethylamino-2-n-pentyloxyphenyl)-3-(1-ethyl-2-methylindol-3-yl)-4-azaphthalide

HRID 1253140Notes

Reaction equation

HRID 1253140 reaction equation
C(OC(=O)C)(=O)C.[C:8]([C:11]1[C:12]([C:17]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH2:28][CH3:29])[C:20]=2[CH3:30])=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=1)(O)=[O:9].[CH2:31]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([N:43]([CH3:45])[CH3:44])[CH:38]=1)[CH2:32][CH2:33][CH2:34][CH3:35].C1(C)C=CC=CC=1>CO>[CH3:44][N:43]([CH3:45])[C:39]1[CH:40]=[CH:41][C:42]([C:17]2([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH2:28][CH3:29])[C:20]=3[CH3:30])[C:12]3[C:11](=[CH:16][CH:15]=[CH:14][N:13]=3)[C:8](=[O:9])[O:18]2)=[C:37]([O:36][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:38]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 1123443-Pyridinecarboxylic acid, 2-((1-ethyl-2-methyl-1H-indol-3-yl)carbonyl)-HCID 201368071-n-Pentyloxy-3-dimethylaminobenzene

Product 1

HCID 141777203-(4-Dimethylamino-2-n-pentyloxyphenyl)-3-(1-ethyl-2-methylindol-3-yl)-4-azaphthalideYield 80.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into 75 ml of acetic anhydride, 9.2 g of (1-ethyl-2-methylindol-3-yl) (3-carboxypyridin-2-yl) ketone and 7050 g of 1-n-pentyloxy-3-dimethylaminobenzene were added, and the resultant mixture was stirred for 4 hours at 60° to 65° C. After cooling the reaction mixture to room temperature, the cooled reaction mixture was poured into 500 ml of ice water and the resultant mixture was treated with toluene and methanol by the same manner as in Synthetic Example 1. As a result, 11.9 g of the objective compound were obtained as pale blue crystals (melting point: 169° to 171° C.). The elementary analytical data of the product were as follows.

Workup

  1. customthe cooled reaction mixture

Sources & evidence

ORD record
ord-0d99a088ec644612bf3d62b212567728
Source dataset
uspto-grants-1988_05
Patent number
US04747875

Reaction notes

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