Sodium Hydroxide → 4-{[3-(Trifluoromethyl)benzyl]amino}quinazoline-8-carboxylic acid

HRID 578627Notes

Reaction equation

HRID 578627 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[C:13]([C:18]([O:20]C)=[O:19])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][N:9]=1.[OH-].[Na+]>CO>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[C:13]([C:18]([OH:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66763817Methyl 4-{[3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxylate

Product 1

HCID 667637834-{[3-(Trifluoromethyl)benzyl]amino}quinazoline-8-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-{[3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxylate (95 mg, 0.26 mmol) in 5 mL of MeOH was treated with 2N NaOH (650 μL, 1.3 mmol, 5 equiv.) under refluxing for 5 h. After removal of MeOH, water was added to the residue and pH was adjusted to ˜4 with 2N HCl. The precipitate was collected as the desired acid by filtration, and washing with water in 89% yield. 1HNMR (in DMSO): 4.96 (d, J=5.8 Hz, 2H), 7.56-7.61 (m, 1H), 7.64 (d, J=7.7 Hz, 1H), 7.70 (d, J=7.7 Hz, 1H), 7.74-7.78 (m, 2H), 8.54 (dd, J=1.2 and 7.4 Hz, 1H), 8.63 (dd, J=1.2 and 7.3 Hz, 1H), 8.69 (s, 1H), 9.68 (d, J=5.8 Hz, 1H). Mass: M+H+: 348.

Workup

  1. temperatureunder refluxing for 5 h
  2. customAfter removal of MeOH, water
  3. additionwas added to the residue and pH
  4. filtrationThe precipitate was collected as the desired acid by filtration
  5. washwashing with water in 89% yield

Sources & evidence

ORD record
ord-e9bd6d219a9b480c8085d1052327eb7c
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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