Ammonia → HCID 86301821, compound

HRID 513968Notes

Reaction equation

HRID 513968 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:18][C:19](OCC)=[O:20])[C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1.[NH3:27]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:18][C:19]([NH2:27])=[O:20])[C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 90417406HCID 90417406, compound

Product 1

HCID 86301821HCID 86301821, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(7-((3-chlorobenzyl)oxy)-2-oxo-1,2-dihydroquinolin-3-yl)acetate (Example 51, product from Step E, 200 mg, 0.54 mmol) was dissolved in a 7 N solution of ammonia in methanol (10 mL) and stirred at room temperature for 2 weeks. The resulting precipitate was collected by filtration, washed with methanol (3 mL) and was dried under vacuum to give the title compound as a white solid (136 mg, 74%). 1H NMR (400 MHz, DMSO-d6) δ 11.68 (s, 1H), 7.70 (s, 1H), 7.54 (s, 2H), 7.43 (s, 3H), 7.35 (br s, 1H), 6.86 (s, 2H), 6.85 (br s, 1H), 5.16 (s, 2H), 3.27 (s, 2H). [M+H]=343.1.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with methanol (3 mL)
  3. customwas dried under vacuum

Sources & evidence

ORD record
ord-65197b9de05c4b2cbb478eaa67130e3a
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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