Acetic Acid → HCID 178526370, compound

HRID 918255Notes

Reaction equation

HRID 918255 reaction equation
[N:1]([O-:3])=O.[Na+].[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[N:15]=[C:14]([NH:16][CH3:17])[CH2:13][N:12]=[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:10]=2[CH:24]=1.C(O)(=O)C>O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[N:15]=[C:14]([NH:16][CH2:17][N:1]=[O:3])[CH2:13][N:12]=[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:10]=2[CH:24]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23668193Sodium NitriteHCID 178482308HCID 178482308, compound

Product 1

HCID 178526370HCID 178526370, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.3 g. (0.0625 mol) of sodium nitrite was added in small portions to a stirred solution of 16.4 g. (0.05 mol) of 7-bromo-2-methylamino-5-(2-pyridyl)-3H-1,4-benzodiazepine in 200 ml. of glacial acetic acid. After addition (15 minutes), the mixture was stirred for 30 minutes at room temperature, diluted with water and extracted with ether. The extracts were washed with saturated sodium bicarbonate solution, dried over sodium sulfate and evaporated, giving crude 7-bromo-2-(N-nitrosomethylamino)-5-(2-pyridyl)-3H-1,4-benzodiazepine as an oil. 2 g. of the remaining oil was chromatographed over 60 g. of silica gel using 10 percent ethanol in methylene chloride. The clean fractions were combined and evaporated. The residue was stirred in isopropanol overnight, whereupon crystalline 7-bromo-2-(N-nitrosomethylamino)-5-(2-pyridyl)-3H-1,4-benzodiazepine separated, m.p. 102°-106°.

Workup

  1. additionAfter addition (15 minutes)
  2. extractionextracted with ether
  3. washThe extracts were washed with saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-e729de1578364b7b92a2eb45b07bf36d
Source dataset
uspto-grants-1976_07
Patent number
US03970664

Reaction notes

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