Ammonium Hydroxide → HCID 70296592, compound

HRID 1421216Notes

Reaction equation

HRID 1421216 reaction equation
[C:1]1([CH:11]=[CH:12][C:13]2[C:19]3[CH:20]=[C:21]([O:26][CH3:27])[C:22]([O:24][CH3:25])=[CH:23][C:18]=3[CH2:17][C:16]([CH3:28])=[N:15][N:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].[OH-].[NH4+]>C(O)(=O)C.O>[C:1]1([CH:11]=[CH:12][C:13]2[C:19]3[CH:20]=[C:21]([O:26][CH3:27])[C:22]([O:24][CH3:25])=[CH:23][C:18]=3[CH2:17][CH:16]([CH3:28])[NH:15][N:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 54459417HCID 54459417, compound

Product 1

HCID 70296592HCID 70296592, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 5.35 g (14.3 mmoles) of 1-[2-(1-naphtyl)-vinyl]-4-methyl-7,8-dimethoxy-5H-2,3-benzodiazepine in 30 ml of glacial acetic acid a solution of 1.76 g (46.3 mmoles) of sodium borohydride in 10 ml of water is dropped at 50° C., under stirring, and the reaction mixture is stirred further for 2 hours. The product is then stirred with 250 ml of water, made alkaline with ammonium hydroxide solution, the separated yellow precipitate is filtered, washed with water and recrystallized from isopropanol. Thus 3.75 g (70.5%) of the desired compound are obtained.

Workup

  1. stirringthe reaction mixture is stirred further for 2 hours
  2. filtrationthe separated yellow precipitate is filtered
  3. washwashed with water
  4. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-7109163f3e6a4e6d958dd142341144dc
Source dataset
uspto-grants-2000_06
Patent number
US06075018

Reaction notes

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