Potassium Hydroxide → HCID 11408176, compound

HRID 748621Notes

Reaction equation

HRID 748621 reaction equation
[CH2:1]([O:8][C:9]1[CH:34]=[CH:33][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:28][CH2:29][CH3:30])=[C:21]([NH:24]C(=O)C)[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:31]#[N:32])=[CH:11][C:10]=1[Cl:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[NH2:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][C:20]=1[O:28][CH2:29][CH3:30])[N:17]=[CH:16][C:15]([C:31]#[N:32])=[C:14]2[NH:13][C:12]1[CH:33]=[CH:34][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([Cl:35])[CH:11]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67315262N-{4-[4-(Benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}acetamide

Product 1

HCID 11408176HCID 11408176, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 298 mg (0.612 mmoles) of the purified N-{4-[4-(benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}acetamide (example 6) and 97 mg (1.73 mmoles) of potassium hydroxide in 10 ml of methanol was stirred and refluxed for 60 hours. On cooling a solid formed. This mixture was poured onto ice, and the resulting solid was filtered and washed with water. On drying, 242 mg of the title compound was obtained.

Workup

  1. temperaturerefluxed for 60 hours
  2. temperatureOn cooling a solid
  3. customformed
  4. additionThis mixture was poured onto ice
  5. filtrationthe resulting solid was filtered
  6. washwashed with water
  7. customOn drying

Sources & evidence

ORD record
ord-53a51f842bac4204a3d5c784f0118e56
Source dataset
uspto-grants-2008_07
Patent number
US07399865B2

Reaction notes

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