Methanol → HCID 22914494, compound

HRID 1378223Notes

Reaction equation

HRID 1378223 reaction equation
[F:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[N:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22].C[O-].[Na+].CO.[Na]>>[NH2:17]/[C:16](=[N:21]\[OH:22])/[C:15]1[N:14]=[CH:13][N:12]2[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[C:7]=3[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]=12

Participants

6

Reactant 5

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 22914615HCID 22914615, compound

Product 1

HCID 22914494HCID 22914494, compound

Procedure

2 g (7.8 mmol) of 7-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile and 1.1 g (15.6 mmol) of hydroxylamine hydrochloride were added to a freshly prepared solution of sodium methylate in methanol (from 0.27 g (11.7 mmol) of sodium in 50 ml of methanol), whereupon the mixture was stirred at room temperature for 16 hours. Subsequently, the suspension was evaporated and treated with 100 ml of water. The precipitate obtained was filtered off and dried in a high vacuum. There were obtained 2 g (89%) of (E)-and/or (Z)-3-(amino-hydroxyimino-methyl)-7-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as a colourless foam, Rf=0.25 (silica gel, methylene chloride/methanol 9:1).

Workup

  1. customSubsequently, the suspension was evaporated
  2. additiontreated with 100 ml of water
  3. customThe precipitate obtained
  4. filtrationwas filtered off
  5. customdried in a high vacuum

Sources & evidence

ORD record
ord-9f693a636aee413e8012746f03d8d0ac
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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