Ethanol → HCID 66851256, compound

HRID 37873Notes

Reaction equation

HRID 37873 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[CH:3]=1.C(O)C.C(N(CC)CC)C>C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=3)[CH2:11][CH2:10]2)[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 668515111-(4,6-Dimethyl-pyridin-2-yl)-4-(4-nitro-phenyl)-[1,4]diazepane

Product 1

HCID 66851256HCID 66851256, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4,6-dimethyl-pyridin-2-yl)-4-(4-nitro-phenyl)-[1,4]diazepane (940 mg, 2.88 mmol) in ethyl acetate (25 mL) was added stannous chloride (3.90 g, 17.3 mmol) and ethanol (5 mL). The reaction mixture was heated to reflux for 15 hours then cooled to room temperature, basified with triethylamine and filtered. The filtrate was concentrated under reduced pressure to afford 4-[4-(4,6-dimethyl-pyridin-2-yl)-[1,4]diazepan-1-yl]-phenylamine (850 mg, 99%) as a brown solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 15 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5d8f74c42ce14871b154b69129200291
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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