Dimethylformamide → HCID 19935434, compound

Reaction equation

P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Na+].CN(C)[CH:22]=[O:23]>>[CH3:6][N:7]1[C:13]2[CH:14]=[CH:15][C:16]([CH:22]=[O:23])=[CH:17][C:12]=2[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 132624261-Methyl-2,3,4,5-tetrahydro-1H-1-benzazepine

Product 1

HCID 19935434HCID 19935434, compound

Conditions

Temperature: 70 °C

Procedure

The starting material was prepared as follows: A. 45 ml of dimethylformamide were treated under an argon atmosphere with 16.2 ml of phosphorus oxychloride. After the reaction had faded away, 7.30 g of 2,3,4,5-tetrahydro-1-methyl-1H-1-benzazepine were added and the reaction mixture was stirred at 70° C. for 5 hours. Thereafter, the mixture was poured on to ice, made alkaline with sodium hydroxide solution, extracted with ether, washed with water, dried and evaporated. Chromatorgraphy on silica gel (petroleum ether/ethyl acetate (87:13)) yielded 4.38 g of 2,3,4,5-tetrahydro-1-methyl-1H-1-benzazepine-7-carboxaldehyde.