Acetic Acid → HCID 67263513, compound

HRID 1041082Notes

Reaction equation

HRID 1041082 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-b21e0eb9d64b49a38f1d48dc3c04f310
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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