Methyl {3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}carbamate → Methyl {3-amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}carbamate

HRID 472943Notes

Reaction equation

HRID 472943 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:18][C:19](=[O:22])[O:20][CH3:21])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)([O-])=O>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:18][C:19](=[O:22])[O:20][CH3:21])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

4

Reactant 1

HCID 57723218Methyl {3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}carbamate

Product 1

HCID 57723219Methyl {3-amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}carbamate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

Methyl {3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}carbamate (2.53 g, 8.18 mmol) was dissolved in 50 mL of EtOAc containing a catalytic amount of 10% Pd/C. The solution was shaken under H2 atmosphere (40 psi) using a Parr hydrogenation apparatus overnight at rt. The solution was filtered through celite and the solvent was evaporated. Yield: 2.29 g (99%). 1H NMR (400 MHz, CHLOROFORM-D): δ 1.40 (ddd, J=25.09, 12.01, 4.49 Hz, 2H), 1.70-1.74 (m, 1 H), 1.74-1.77 (m, 1H), 1.81-1.92 (m, 1H), 2.99 (d, J=6.64 Hz, 2H), 3.34 (br.s, 2 H), 3.41 (dt, J=11.81, 2.15 Hz, 2H), 3.74 (s, 3H), 3.99 (d, J=3.51 Hz, 1H), 4.02 (d, J=3.51 Hz, 1H), 6.38 (br.s, 1H), 6.55-6.60 (m, 1H), 6.62-6.68 (m, 1H), 6.95 (br.s, 1H).

Workup

  1. customa Parr hydrogenation apparatus overnight
  2. customat rt
  3. filtrationThe solution was filtered through celite
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d2e2896fdf1f44949cfab1d96dd879f2
Source dataset
uspto-grants-2014_01
Patent number
US08633235B2

Reaction notes

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