Sodium Hydroxide → HCID 57938787, compound

HRID 1436293Notes

Reaction equation

HRID 1436293 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 vaccum, 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 vaccum
  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-1ce2f494c5ea42faa5e87138e3d2918b
Source dataset
uspto-grants-2009_11
Patent number
US07618975B2

Reaction notes

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