Sodium Hydroxide → HCID 57938787, compound

HRID 1876131Notes

Reaction equation

HRID 1876131 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([C:21]([O:23]CC)=[O:22])[N:12]=2)[CH3:10])=[CH:5][CH:4]=1.[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([C:21]([OH:23])=[O:22])[N:12]=2)[CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11163523HCID 11163523, compound

Product 1

HCID 57938787HCID 57938787, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 4-(N-(4-methoxy-phenyl)-N-methylamino)quinazoline-2-carboxylate (560 mg, 1.66 mmol) and sodium hydroxide (126 mg, 3.15 mmol) in 25 mL of methanol and water (1:3) was stirred at room temperature for 5 h. The solvents were removed under vacuum, and the residue was dissolved in 50 mL of water and acidified to pH 3. The white precipitate was collected and washed with water and dried (380 mg, 1.23 mmol, 74%). 1H NMR (CDCl3): 8.02-8.05 (m, 1H), 7.68 (ddd, J=1H, 8.4, 6.9, 1.5), 7.14-7.20 (m, 3H), 7.02-7.05 (m, 1H), 6.94-6.99 (m, 2H), 3.87 (s, 3H), 3.74 (s, 3H).

Workup

  1. customThe solvents were removed under vacuum
  2. dissolutionthe residue was dissolved in 50 mL of water
  3. customThe white precipitate was collected
  4. washwashed with water
  5. customdried (380 mg, 1.23 mmol, 74%)

Sources & evidence

ORD record
ord-a23a068fcd0f4a1e9baaa18e6498ccf0
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

Loading…