3-Nitroaniline → HCID 90052093, compound

HRID 2284674Notes

Reaction equation

HRID 2284674 reaction equation
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+:16]([C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22])([O-:18])=[O:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(OCC)(=O)C.C(O)(=O)C>[N+:16]([C:19]1[CH:20]=[C:21]([NH:22][CH:11]2[CH2:12][CH2:13][CH2:14][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]2)[CH:23]=[CH:24][CH:25]=1)([O-:18])=[O:17]

Participants

8

Reactant 4

HCID 74233-NitroanilineHCID 516892Sodium BicarbonateHCID 1512679N-Boc-hexahydro-1H-azepin-4-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 90052093HCID 90052093, compoundYield 71.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-Boc-hexahydro-1H-azepin-4-one (141 mg) and 3-nitroaniline (91 mg) in methylene chloride (3 mL), sodium triacetoxyborohydride (210 mg) and acetic acid (38 μL) were added at room temperature, and the mixture was stirred at the same temperature for 10 hours. To the reaction mixture, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 30% hexane in ethyl acetate) to obtain tert-butyl 4-((3-nitrophenyl)amino)azepane-1-carboxylate (C25, 157 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 30% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-d3a79e311bfc4b8bbae8b6c9c55a74b9
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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