Acetic Acid → 7-Nitro-3-(propan-2-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2174709Notes

Reaction equation

HRID 2174709 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH3:15][C:16]([CH3:18])=O.C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1>[CH:16]([N:10]1[CH2:11][CH2:12][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:14]=[CH:13][C:7]=2[CH2:8][CH2:9]1)([CH3:18])[CH3:15]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 113100427-Nitro-2,3,4,5-tetrahydro-1H-benzo[D]azepine

Product 1

HCID 674558787-Nitro-3-(propan-2-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.96 g (5.00 mmol) 7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine and 0.404 ml (5.50 mmol) acetone are dissolved in 20 ml THF, then 0.414 ml (7.50 mmol) acetic acid and 0.10 g p-toluenesulphonic acid are added and the mixture is stirred for 30 min at room temperature. At room temperature 1.378 g (6.50 mmol) sodium triacetoxyborohydride are added and stirred for 23 h. Then the mixture is made alkaline with sat. Sodium hydrogen carbonate solution and extracted with ethyl acetate, then the organic phase is dried with sodium sulphate and concentrated by evaporation i.vac.

Workup

  1. stirringstirred for 23 h
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase is dried with sodium sulphate
  4. concentrationconcentrated by evaporation i.vac

Sources & evidence

ORD record
ord-301713b973b34a369de3f8b917a13d22
Source dataset
uspto-grants-2015_06
Patent number
US09062034B2

Reaction notes

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