Sodium Chloride → 7-Amino-1,1-dimethyl-1,2,4,5-tetrahydrobenzo[c]azepin-3-one

HRID 1688116Notes

Reaction equation

HRID 1688116 reaction equation
[CH3:1][C:2]1([CH3:17])[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-])=O)=[CH:12][C:7]=2[CH2:6][CH2:5][C:4](=[O:16])[NH:3]1.[O-]S(S([O-])=O)=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Na+].[Cl-]>C1COCC1.CO.O.CCOC(C)=O>[NH2:13][C:11]1[CH:10]=[CH:9][C:8]2[C:2]([CH3:17])([CH3:1])[NH:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]=2[CH:12]=1

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 672644211,1-Dimethyl-7-nitro-1,2,4,5-tetrahydrobenzo[c]azepin-3-one

Product 1

HCID 672644267-Amino-1,1-dimethyl-1,2,4,5-tetrahydrobenzo[c]azepin-3-oneYield 26.2%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,1-dimethyl-7-nitro-1,2,4,5-tetrahydrobenzo[c]azepin-3-one (1.75 g) in THF (175 mL) and MeOH (20 mL) was treated with an solution of Na2S2O4 (5 g) and sodium bicarbonate (5 g) in water (200 mL). After 15 minutes, 250 mL of EtOAc and 250 mL saturated NaCl was added and the organic layer was separated. The aqueous layer was extracted again with EtOAc and the combined organic layers were washed again with brine. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo to provide 400 mg of 7-amino-1,1-dimethyl-1,2,4,5-tetrahydrobenzo[c]azepin-3-one: 1H NMR (300 MHz, CDCl3) δ 7.1 (d, 1H, C9-H), 6.5 (dd, 1H, C8-H), 6.4 (d, 1H, C6-H), 3.0 (m, 2H), 2.6 (m, 2H), 1.6 (s, 6H).

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted again with EtOAc
  3. washthe combined organic layers were washed again with brine
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3fd9db9d00814a41a38f90e888ae63c6
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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