Phenyl methyl(2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate → Phenyl 2-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate

HRID 1922403Notes

Reaction equation

HRID 1922403 reaction equation
[CH3:1][N:2]([CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][C:20]([N+:24]([O-])=O)=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1)[C:3](=[O:11])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[H][H]>[Pd].C1COCC1.CCO>[NH2:24][C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[N:14]([CH2:13][CH2:12][N:2]([CH3:1])[C:3](=[O:11])[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:15][CH2:16][CH2:17]2

Participants

5

Reactant 2

HCID 57343232Phenyl methyl(2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 57343723Phenyl 2-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A suspension of phenyl methyl(2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate (500 mg, 1.41 mmol) and palladium on activated carbon (10%, 75 mg, 0.07 mmol) in a 1:1 mixture of THF/EtOH (20 mL) was stirred under a balloon of hydrogen for 4.5 hours. The suspension was filtered through a pad of celite. The filter pad was rinsed with 25 mL methanol and the filtrate was concentrated to give a dark viscous oil. The crude product was used without further purification (460 mg, quantitative). 1H-NMR (CDCl3) δ 7.39-7.34 (m, 2H), 7.22-7.17 (m, 1H), 7.12-7.08 (m, 2H), 6.61-6.42 (m, 3H), 3.61-3.45 (m, 4H), 3.26 (t, J=6.0 Hz, 2H), 3.20 (brs, 2H), 3.13 and 3.06 (2×s, 3H), 2.70 (t, J=6.3 Hz, 2H), 1.96-1.87 (m, 2H). MS (ESI): 326.2 (M+1).

Workup

  1. filtrationThe suspension was filtered through a pad of celite
  2. washThe filter pad was rinsed with 25 mL methanol
  3. concentrationthe filtrate was concentrated
  4. customto give a dark viscous oil
  5. customThe crude product was used without further purification (460 mg, quantitative)

Sources & evidence

ORD record
ord-24b023dfc75344ae8b12271a7a91839a
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…