HCID 69083292, compound → HCID 69081808, compound

HRID 594661Notes

Reaction equation

HRID 594661 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[C:3]=1[CH:13]1[N:18]([CH2:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)[C:17](=[O:30])[CH2:16][CH2:15][CH2:14]1>CO>[NH2:8][C:7]1[C:2]([OH:1])=[C:3]([CH:13]2[N:18]([CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)[C:17](=[O:30])[CH2:16][CH2:15][CH2:14]2)[C:4]([O:11][CH3:12])=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 69083292HCID 69083292, compound

Product 1

HCID 69081808HCID 69081808, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-(2-hydroxy-6-methoxy-3-nitrophenyl)-1-(quinolin-2-ylmethyl)piperidin-2-one (340 mg; 0.83 mmol), and 10% Pd(C) (34 mg; 10% in mass) in anh. MeOH (15 ml) was stirred at rt, under hydrogen atmosphere (1 atm), for 5.5 h. Filtration over a pad of celite, concentration to dryness under reduced pressure, and additional drying under HV afforded 6-(3-amino-2-hydroxy-6-methoxyphenyl)-1-(quinolin-2-ylmethyl)piperidin-2-one as a red solid (302 mg; 96%). LC-MS (conditions A): tR=0.41 min.; [M+H]+: 378.38 g/mol.

Workup

  1. filtrationFiltration
  2. concentrationover a pad of celite, concentration to dryness under reduced pressure
  3. customadditional drying under HV

Sources & evidence

ORD record
ord-791fe728391c453fb65968871f551849
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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