Methane → tert-butyl N-[(4-aminophenyl)methyl]carbamate

HRID 1290526Notes

Reaction equation

HRID 1290526 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H].C>[Pd].C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 297MethaneHCID 10610803tert-Butyl 4-nitrobenzylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% w/w palladium on charcoal (250 mg) was added to a solution of the product from step i) (5.37 g) in ethanol (100 ml) and the mixture hydrogenated at room temperature and pressure until the theoretical amount of hydrogen had been taken up. Charcoal was added, the mixture stirred for 10 minutes then filtered through diatomaceous earth and the filtrate evaporated to dryness. The solid residue, on recrystallisation from ethyl acetate/hexane gave 4-(N-tertiary-butyloxycarbonylaminomethyl)aniline, 4.20 g; m.p. 80°-82° C.; NMR (d6DMSO) δ7.10(1H,bt), 6.88(2H,d), 6.49(2H,d), 4.92(2H,s), 3.92(2H,d), 1.38(9H,s); m/e 223(M+H)+ ; calculated for C12H18N2 O2 : C, 64.8; H, 8.2; N, 12.6. found: C, 65.4; H, 8.3; N, 13.0%.

Workup

  1. customhydrogenated at room temperature
  2. filtrationthen filtered through diatomaceous earth
  3. customthe filtrate evaporated to dryness
  4. customThe solid residue, on recrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-183eb00231534156b8d92d8f9a7be99d
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

Loading…