Phthalimide potassium salt → tert-Butyl 4-(aminomethyl)-3-nitrobenzylcarbamate

HRID 1296772Notes

Reaction equation

HRID 1296772 reaction equation
Br[CH2:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:5][C:4]=1[N+:18]([O-:20])=[O:19].C1(=O)[NH:25]C(=O)C2=CC=CC=C12.[K]>CN(C=O)C.C(OCC)(=O)C.C1(=O)NC(=O)C2=CC=CC=C12.[K]>[NH2:25][CH2:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:5][C:4]=1[N+:18]([O-:20])=[O:19]

Participants

6

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 86595904tert-Butyl 4-(bromomethyl)-3-nitrobenzylcarbamate

Product 1

HCID 86595905tert-Butyl 4-(aminomethyl)-3-nitrobenzylcarbamateYield 118.9%

Reagents, catalysts & solvents 3

HCID 24194345Phthalimide potassium saltCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of compound 65b (1.08 g, 3.11 mmol) and potassium phthalimide (0.634 g) in DMF (10 mL) was stirred at rt overnight. Additional potassium phthalimide (0.063 g) was added and stirring was continued for 4 h. The reaction was diluted with ethyl acetate, washed with water and brine, dried, and concentrated. The residue was dissolved in ethanol (20 mL) and hydrazine (0.34 mL) was added. The reaction mixture was refluxed for 1 h, and then cooled and filtered. The filtrate was concentrated to give compound 65c (1.04 g). ESI-MS m/e 282 (M+1).

Workup

  1. stirringstirring
  2. waitwas continued for 4 h
  3. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethanol (20 mL)
  7. additionhydrazine (0.34 mL) was added
  8. temperatureThe reaction mixture was refluxed for 1 h
  9. temperaturecooled
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-cde67d81a6e84964a97abe9aff560c90
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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