Acetic Acid → HCID 67263513, compound

HRID 1687387Notes

Reaction equation

HRID 1687387 reaction equation
[CH3:1][O:2][C:3]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[CH3:17][C:18]([CH3:20])=O.C(O)(=O)C.CO.C([BH3-])#N.[Na+]>>[CH:18]([N:9]1[CH2:10][CH2:11][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:6]=2[CH2:7][CH2:8]1)([CH3:20])[CH3:17]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 672643517-Methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 67263513HCID 67263513, compound

Procedure

To a solution of 7-Methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.15 g, 0.00067 mol), Acetone (0.10 mL, 0.0014 mol), Acetic acid (0.1 mL, 0.002 mol) and Methanol (10 mL, 0.2 mol) was added Sodium cyanoborohydride (50 mg, 0.0008 mol). The mixture was stirred at room temperature for 4 hours. The reaction mixture was evaporated and the residue was partitioned between water (20 mL) and dichloromethane (20 mL). The organic layers were dried over magnesium sulfate, filtered and evaporated. The mixture was purified via silica gel chromatography using amine modified silica gel 10%→100% Ethyl Acetate:Hexane solvent gradient. 3-Isopropyl-7-methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine isolated as a yellow oil.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between water (20 mL) and dichloromethane (20 mL)
  3. dry with materialThe organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe mixture was purified via silica gel chromatography

Sources & evidence

ORD record
ord-9a11c4f081204d6ca620f05e1bc8a17e
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…