Ammonia → HCID 86301820, compound

HRID 1748416Notes

Reaction equation

HRID 1748416 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]([CH2:11][CH: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]([CH2:11][CH: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 90416764Ethyl 2-(7-((3-chlorobenzyl)oxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate

Product 1

HCID 86301820HCID 86301820, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(7-((3-chlorobenzyl)oxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate (Example 51, product from Step D, 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 (111 mg, 60%). 1H NMR (400 MHz, DMSO-d6) δ 10.08 (s, 1H), 7.53-7.33 (m, 5H), 7.06 (d, J=8.3 Hz, 1H), 6.85 (br s, 1H), 6.57 (dd, J=2.4, 8.3 Hz, 1H), 6.51 (d, J=2.4 Hz, 1H), 5.05 (s, 2H), 2.93-2.70 (m, 2H), 2.71-2.54 (m, 2H), 2.11 (dd, J=8.5, 15.2 Hz, 1H). [M+H]=345.1.

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-e5988e04c9914dba9e841862a92dca71
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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