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

HRID 1291879Notes

Reaction equation

HRID 1291879 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°-81° C.; NMR (d6DMSO) δ 7.10(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 C12H18N2O2 : 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-539b0b4da5ab40cf9a02ae03b7a0910e
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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