Ammonia → HCID 86296661, compound

HRID 1748404Notes

Reaction equation

HRID 1748404 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-8610a9fec65d4c87ac40a0bdda9d54ac
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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