Benzylamine → Ammonia

HRID 2118355Notes

Reaction equation

HRID 2118355 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]2[CH2:22][O:21]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[NH3:17].[CH2:23]([NH:30][CH2:22][C@@H:20]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:19])[NH:17]2)[OH:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 114378125-(2R)-2-Oxiranyl-8-(phenylmethoxy)-2(1H)-quinolinone

Product 2

HCID 222AmmoniaHCID 691197205-[(1R)-2-(Benzylamino)-1-hydroxyethyl]-8-(benzyloxy)quinolin-2(1H)-one

Procedure

8-(Benzyloxy)-5-[(2R)-oxiran-2-yl]quinolin-2(1H)-one (0.102 g) (WO 9525104), was dissolved in benzylamine (0.5 ml) and heated in a microwave oven for 15 min at 150°. Excess benzylamine was removed by evaporation on a rotary evaporator and the residue was purified on a silica SPE bond elut cartridge using MeOH/DCM-0.880 ammonia mixtures, to give the title compound (106 mg). LCMS RT=2.30 min

Workup

  1. temperatureheated in a microwave oven for 15 min at 150°
  2. customExcess benzylamine was removed by evaporation on a rotary evaporator
  3. customthe residue was purified on a silica SPE bond elut cartridge

Sources & evidence

ORD record
ord-880ac37b3955411491cae66a6889f58c
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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