Ammonium Hydroxide → HCID 86301654, compound

HRID 513958Notes

Reaction equation

HRID 513958 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19])[CH:13]=[N:14]2)=[CH:9][CH:8]=1.[OH-].[NH4+:27]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]([CH3:22])([CH3:21])[C:18]([NH2:27])=[O:19])[CH:13]=[N:14]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 90416631HCID 90416631, compound

Product 1

HCID 86301654HCID 86301654, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(7-((3-chlorobenzyl)oxy)quinolin-3-yl)-2-methylpropanoyl chloride in THF (3 mL) was added ammonium hydroxide (10 mL). The reaction was stirred overnight at ambient temperature. The reaction mixture was concentrated onto silica and purification (FCC, SiO2, 0-10%, MeOH/DCM) afforded the title compound as a white solid (28 mg, 10%). 1H NMR (400 MHz, CDCl3) δ 8.88 (d, J=2.7 Hz, 1H), 8.07 (d, J=2.3 Hz, 1H), 7.73 (d, J=9.0 Hz, 1H), 7.49 (s, 1H), 7.45 (d, J=2.3 Hz, 1H), 7.39-7.27 (m, 4H), 5.34-5.22 (m, 2H), 5.19 (s, 2H), 1.71 (s, 6H). [M+H]=355.3.

Workup

  1. concentrationThe reaction mixture was concentrated onto silica and purification (FCC, SiO2, 0-10%, MeOH/DCM)

Sources & evidence

ORD record
ord-8fcab50153f144ca95535ea655686ad8
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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