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

HRID 864840Notes

Reaction equation

HRID 864840 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) 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 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-37b3a9260c2c49c7ad7b8cd9430c2ee3
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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