Water → ethyl 4,5-dihydro-4-methyl-5-oxo-3H-1,4-benzodiazepine-2-glyoxylate alpha-oxime

HRID 67564Notes

Reaction equation

HRID 67564 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[NH:5][C:4](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=O)[CH2:3]1.[N:20]([O-])=[O:21].[Na+].[OH2:24]>C(O)(=O)C>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]=[C:4]([C:14](=[O:24])[C:15](=[N:20][OH:21])[O:17][CH2:18][CH3:19])[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 86738265HCID 86738265, compound

Product 1

HCID 86738266ethyl 4,5-dihydro-4-methyl-5-oxo-3H-1,4-benzodiazepine-2-glyoxylate alpha-oxime

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

32.2 g (0.124 mol) of ethyl (1,3,4,5-tetrahydro-4-methyl-5-oxo-2H-1,4-benzodiazepin-2-ylidene)acetate are dissolved in 300 ml of acetic acid and treated at room temperature with 12.8 g (0.186 mol) of sodium nitrite. The mixture is stirred at room temperature for a further 10 minutes, then poured into 1 liter of water and extracted three times with 200 ml of chloroform each time. The combined chloroform phases are washed with 100 ml of water, dried over magnesium sulphate and evaporated. The residue is recrystallised from ethyl acetate. There is obtained ethyl 4,5-dihydro-4-methyl-5-oxo-3H-1,4-benzodiazepine-2-glyoxylate α-oxime of melting point 173°-174° C.

Workup

  1. extractionextracted three times with 200 ml of chloroform each time
  2. washThe combined chloroform phases are washed with 100 ml of water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-f7d69fa77c4544acacb4a99dda7d751f
Source dataset
uspto-grants-1982_08
Patent number
US04346035

Reaction notes

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