Acetic Acid → HCID 67263880, compound
Reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][C:6]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:7]=1[C:8]#N.[CH3:17]C(C[AlH]CC(C)C)C.CC(O)=O.C([BH3-])#N.[Na+]>C(Cl)Cl.C1COCC1.O>[CH2:1]([N:2]1[CH2:8][C:7]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:6]=2[NH:5][CH2:4][CH2:3]1)[CH3:17]Participants
Procedure
A solution of 2-(2-methylamino-ethylamino)-4-nitro-benzonitrile (1 g) in methylene chloride (100 mL) was cooled to −78° C. and treated with 1 M DIBAL-H in hexanes (8.5 mL). The mixture was allowed to slowly warm to room temperature and stirred for 16 hours. The mixture was treated with HOAc (2 mL) followed by 1 M sodium cyanoborohydride in THF (4 mL). After 1 hour, the mixture was diluted with water and the organic layer was separated. The aqueous phase was extracted again with methylene chloride and the combined organics were dried over sodium sulfate, filtered and concentrated. Silica gel chromatography (1→2% MeOH/methylene chloride) provided 4-ethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine, which was heated in acetic anhydride at 100° C. for 2 hours to provide, after concentration and silica gel chromatography 1-(4-ethyl-8-nitro-2,3,4,5-tetrahydro-benzo[e][1,4]diazepin-1-yl)-ethanone (90 mg).
Workup
- waitAfter 1 hour
- customthe organic layer was separated
- extractionThe aqueous phase was extracted again with methylene chloride
- dry with materialthe combined organics were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4c70f3cedc4d44afba2a8bde07c2c982
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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