Ammonium Hydroxide → HCID 86301654, compound

HRID 1748408Notes

Reaction equation

HRID 1748408 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-275e709afd534d06ba122735e766a6aa
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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