Potassium Hydroxide → 2-Carboxy-5,6-dihydropyrrolo[1,2-c]quinazoline-6-propionic acid

HRID 65925Notes

Reaction equation

HRID 65925 reaction equation
Cl.C([O:4][C:5](=[O:26])[CH2:6][CH2:7][N:8]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2=[CH:18][C:19]([C:21]([O:23]CC)=[O:22])=[CH:20][N:10]2[CH2:9]1)C.[OH-].[K+]>CO.O>[C:21]([C:19]1[CH:18]=[C:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[N:8]([CH2:7][CH2:6][C:5]([OH:26])=[O:4])[CH2:9][N:10]2[CH:20]=1)([OH:23])=[O:22]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 70615356HCID 70615356, compound

Product 1

HCID 227563532-Carboxy-5,6-dihydropyrrolo[1,2-c]quinazoline-6-propionic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of the product of Example VI (2.75 g, 0.008 m) and KOH (4.0 g, 0.072 m) in MeOH (40 ml) and H2O (40 ml) was refluxed for 4 hr. The methanol was removed under vacuum and the resulting aqueous solution was acidified with HCl (10% aqueous). When the solution became acidic, a greenish solid formed. It was filtered and washed with H2O and dried, to yield 2.2 g of crude product. Crystallization from MeOH afforded the desired product; m.p. 234°-236°.

Workup

  1. customThe methanol was removed under vacuum
  2. customa greenish solid formed
  3. filtrationIt was filtered
  4. washwashed with H2O
  5. customdried
  6. customto yield 2.2 g of crude product
  7. customCrystallization from MeOH

Sources & evidence

ORD record
ord-0627748087254cf4875a4cd883658e56
Source dataset
uspto-grants-1978_12
Patent number
US04129653

Reaction notes

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