Ammonia → HCID 86296661, compound

HRID 513954Notes

Reaction equation

HRID 513954 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]([CH2:17][C:18](OCC)=[O:19])[CH:13]=[N:14]2)=[CH:9][CH:8]=1.CCOCC.[NH3:31]>CO>[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]([CH2:17][C:18]([NH2:31])=[O:19])[CH:13]=[N:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 86296662HCID 86296662, compound

Product 1

HCID 86296661HCID 86296661, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(7-((3-chlorobenzyl)oxy)quinolin-3-yl)acetate (Example 51, 100 mg, 0.28 mmol) was dissolved in a 7N solution of ammonia in MeOH (40 mL) and stirred at ambient temperature overnight. The reaction mixture was concentrated under reduced pressure to afford a yellow solid. Et2O was added and the yellow precipitate was collected by filtration. DCM was added and the off white precipitate was isolated by filtration, this was repeated to yield the title compound as an off white solid (59 mg, 64%). 1H NMR (400 MHz, DMSO-d6) δ 8.74 (d, J=2.0 Hz, 1H), 8.14 (d, J=2.0 Hz, 1H), 7.92 (d, J=9.0 Hz, 1H), 7.64 (d, J=1.6 Hz, 2H), 7.57-7.44 (m, 4H), 7.37 (dd, J=2.7, 9.0 Hz, 1H), 7.08-7.02 (m, 1H), 5.34 (s, 2H), 3.60 (s, 2H). [M+H]=327.2.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford a yellow solid
  3. filtrationthe yellow precipitate was collected by filtration
  4. additionDCM was added
  5. customthe off white precipitate was isolated by filtration

Sources & evidence

ORD record
ord-c2a2da6eb8a54549854a40743ad4be8e
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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