Hydrochloric Acid → 2-Carbethoxy-5-methyl-5,6-dihydropyrrolo[1,2-c]quinazoline

HRID 65929Notes

Reaction equation

HRID 65929 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([CH3:18])[N:9]2[CH:19]=1)([O:3][CH2:4][CH3:5])=[O:2].Cl.[BH3-]C#N.[Na+]>CCO.CO>[C:1]([C:6]1[CH:7]=[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:11][CH:10]([CH3:18])[N:9]2[CH:19]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 227563512-Carbethoxy-5-methylpyrrolo[1,2-c]quinazoline

Product 1

HCID 227563592-Carbethoxy-5-methyl-5,6-dihydropyrrolo[1,2-c]quinazoline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

The product of Example XXXVI (14.0 g, 0.0436 m) was dissolved in EtOH (1.5 lit) and the pH was adjusted to 4 with methanolic HCl. A solution of NaBH3CN (18.0 g, 0.272 m) in MeOH (300 ml) was added. The pH was readjusted to 4 at 5 min intervals for 20 min. After this time, the pH remained at 4. The reaction mixture was stirred at ambient temperature for 2 hr. The solvent was removed and the residue slurried in H2O (250 ml) and treated with 1N NaOH until basic. The mixture was extracted with CH2Cl2 (2 × 200 ml). The organic extract was dried over Na2SO4, filtered, and the solvent removed to give a white solid; m.p. 102°-103° C.

Workup

  1. waitintervals for 20 min
  2. customThe solvent was removed
  3. additionthe residue slurried in H2O (250 ml) and treated with 1N NaOH until basic
  4. extractionThe mixture was extracted with CH2Cl2 (2 × 200 ml)
  5. extractionThe organic extract
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto give a white solid

Sources & evidence

ORD record
ord-fa03c6702fe8459396d17ecdea1e82f3
Source dataset
uspto-grants-1978_12
Patent number
US04129653

Reaction notes

Loading…