Sodium Hydroxide → HCID 21973691, compound

HRID 11855

Reaction equation

HRID 11855 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21973698Methyl 4-(8-quinolylaminomethyl)benzoate

Product 1

HCID 21973691HCID 21973691, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 16-1 (1 g) was dissolved in methanol (10 ml), and 1 mol/l aqueous solution of sodium hydroxide (10 ml) was added. The reaction solution was dissolved in THF (10 ml). After the reaction for 7 hours, the reaction solution was concentrated. The obtained residue was dissolved in water and 1 mol/l hydrochloric acid was gradually added while stirring to obtain a precipitate. The precipitate was collected by filtration through glass filter G4 and washed with water to obtain the title compound (560.1 mg) as a pale yellow solid.

Workup

  1. customAfter the reaction for 7 hours
  2. concentrationthe reaction solution was concentrated
  3. dissolutionThe obtained residue was dissolved in water
  4. addition1 mol/l hydrochloric acid was gradually added
  5. customto obtain a precipitate
  6. filtrationThe precipitate was collected by filtration through glass
  7. filtrationfilter G4
  8. washwashed with water

Sources & evidence

ORD record
ord-333a087240e745fe8e998f895bad03a7
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Linked notes

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