Water → HCID 13280937, compound

HRID 1903635Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][N:5]1[C:14]([CH3:15])=[C:13]2[C:7]([CH2:8][N:9]=[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:11]3[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:12]=32)=[CH:6]1.[H-].[Al+3].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[Cl:20][C:18]1[CH:17]=[CH:16][C:12]2[C:13]3[C:7](=[CH:6][N:5]([CH2:4][CH2:3][OH:2])[C:14]=3[CH3:15])[CH2:8][N:9]=[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:11]=2[CH:19]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 4.0 g (9.6 mmol) of 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-acetic acid methyl ester in 40 ml of tetrahydrofuran was added dropwise to a solution of 0.8 g (21.0 mmol) of lithuium aluminum hydride in 50 ml of tetrahydrofuran which was cooled to -78° C. When the addition was complete, the reaction mixture was allowed to warm to 0° C. and stirred for 30 minutes. The mixture was treated with 1 ml of water, 1 ml of a 3 N solution of aqueous sodium hydroxide and 3 ml of water. The resulting precipitate was removed by filtration, and the filtrate was concentrated at reduced pressure. The residue crystallized from ether to yield 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-ethanol as pale yellow prisms, mp 149°-152° C. Recrystallization from a mixture of ether and methylene chloride gave white prisms, mp 151°-153° C.

Workup

additionWhen the addition
temperatureto warm to 0° C.
customThe resulting precipitate was removed by filtration
concentrationthe filtrate was concentrated at reduced pressure
customThe residue crystallized from ether

Sources & evidence

ORD record: ord-68b8f786bf2f427eb350d37c8872365b
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04436662

Reaction notes

Loading…