Water → HCID 9811219, compound

HRID 2232547Notes

Reaction equation

HRID 2232547 reaction equation
[CH3:1][CH:2]([C:8](OCC)=O)[C:3]([O:5]CC)=[O:4].[H-].[Na+].BrC[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:18]=1.O>O1CCCC1>[CH3:1][CH:2]([CH2:8][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:18]=1)[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11857Diethyl methylmalonateHCID 24758Sodium hydrideHCID 13769246HCID 13769246, compound

Product 1

HCID 9811219HCID 9811219, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of diethyl methylmalonate (23 g) in anhydrous tetrahydrofuran (100 cc) is added under nitrogen to sodium hydride (4 g, 80% strength in oil) and anhydrous tetrahydrofuran (60 cc). After 1 hour's stirring, a solution of 4-bromomethyl-2-phenylquinazoline (9.9 g) in anhydrous tetrahydrofuran (100 cc) is added, and the mixture is stirred for a further 2 hours at room temperature (approximately 20° C.). Water (100 cc) is added and the mixture is extracted with ethyl acetate (3×100 cc). The organic phase is dried over magnesium sulphate and then evaporated to dryness under reduced pressure. The residue is taken up in concentrated hydrochloric acid (100 cc) and acetic acid (100 cc) and the mixture is brought to 110° C. for 24 hours. After the mixture has cooled, the precipitate is filtered off and washed with water and then ispropyl ether. After being dried, α-methyl-2-phenyl-4-quinazolinepropanoic acid (4 g), m.p. 180° C., is obtained.

Workup

  1. stirringthe mixture is stirred for a further 2 hours at room temperature (approximately 20° C.)
  2. extractionthe mixture is extracted with ethyl acetate (3×100 cc)
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated to dryness under reduced pressure
  5. waitacetic acid (100 cc) and the mixture is brought to 110° C. for 24 hours
  6. temperatureAfter the mixture has cooled
  7. filtrationthe precipitate is filtered off
  8. washwashed with water
  9. customAfter being dried

Sources & evidence

ORD record
ord-ef87bff669c94270978950e11f03cc64
Source dataset
uspto-grants-1988_11
Patent number
US04788204

Reaction notes

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