Sodium Hydroxide → HCID 59509410, compound

HRID 554484Notes

Reaction equation

HRID 554484 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[C:10]2[O:15][C:16]1[CH:17]=[C:18]([N:23](C(C)(C)C)C(=O)[O-])[CH:19]=[CH:20][C:21]=1[CH3:22])(=[O:3])[CH3:2].[OH-].[Na+]>ClCCl.FC(F)(F)C(O)=O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[C:10]2[O:15][C:16]1[CH:17]=[C:18]([NH2:23])[CH:19]=[CH:20][C:21]=1[CH3:22])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86645918HCID 86645918, compound

Product 1

HCID 59509410HCID 59509410, compoundYield 107.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3-(8-Acetylaminoquinolin-4-yloxy)-4-methylphenyl-t-butylcarbamate (120 mg, 0.26 mmol) was dissolved in a 1:1 (by volume) mixture of dichloromethane and trifluoroacetic acid, which was then stirred at room temperature for one hour. When the reaction was completed, the resultant was neutralized with 1 M sodium hydroxide. The resultant was extracted with dichloromethane and water, and combined organic layers were dried with anhydrous sodium sulfate, and then filtered. After the solvent was removed by vacuum distillation, filtered a brown solid product to obtain 86 mg of the desired compound (yield 88.6%).

Workup

  1. extractionThe resultant was extracted with dichloromethane and water
  2. dry with materialwere dried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. customAfter the solvent was removed by vacuum distillation
  5. filtrationfiltered a brown solid product

Sources & evidence

ORD record
ord-d71461e4963648919416350a5c215427
Source dataset
uspto-grants-2011_11
Patent number
US08049014B2

Reaction notes

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