Nitric Acid → HCID 59150535, compound

HRID 1668591Notes

Reaction equation

HRID 1668591 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:23]=[CH:22][C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14][C:8]=2[C:7]=1[CH3:24].C(Cl)Cl.CO.[NH4+].[OH-]>C(Cl)Cl>[OH:5][C:6]1[C:23]([N+:1]([O-:4])=[O:2])=[CH:22][C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH2:13][CH2:14][C:8]=2[C:7]=1[CH3:24]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 14923Ammonium HydroxideHCID 21226129Dichloromethane methanolHCID 57505967HCID 57505967, compound

Product 1

HCID 59150535HCID 59150535, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Nitric acid (65%, 0.370 ml) was added dropwise with vigorous stirring to 1,1-dimethylethyl 7-hydroxy-6-methyl-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (600 mg) and silica gel (1.67 g) in DCM (5.7 ml) at −15° C. After 30 min a mixture of DCM/MeOH/conc.NH4OH: 10/3/1.5 was added and silica gel was filtered off. The solvent was evaporated under reduced pressure and the residue was purified on silica gel (ethyl acetate/petroleum ether: 15/85) obtaining the desired compound (470 mg, 67% yield).

Workup

  1. filtrationsilica gel was filtered off
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified on silica gel (ethyl acetate/petroleum ether: 15/85)

Sources & evidence

ORD record
ord-66326866d8e94465b96685838e4162ad
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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