Acetic Acid → HCID 67263880, compound

HRID 1688152Notes

Reaction equation

HRID 1688152 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

8

Reactant 4

HCID 176Acetic AcidHCID 14487Diisobutylaluminum hydrideHCID 5003444Sodium cyanoborohydrideHCID 67263777HCID 67263777, compound

Product 1

HCID 67263880HCID 67263880, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

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

  1. waitAfter 1 hour
  2. customthe organic layer was separated
  3. extractionThe aqueous phase was extracted again with methylene chloride
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-71dff66879fd453db3a9f32b729c7b3d
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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