Hydrochloric Acid → HCID 53937337, compound

HRID 2296354Notes

Reaction equation

HRID 2296354 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[CH2:15][CH2:16][CH2:17][N:3]12.[CH3:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O.C[O-].[Na+].Cl>CO>[CH3:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=[C:15]1[C:4]2=[N:5][C:6]3[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[CH:10][C:11]=3[C:2](=[O:1])[N:3]2[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 107222-MethylbenzaldehydeHCID 10942334Sodium MethoxideHCID 123440169-Oxo-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline-7-carboxylic acid

Product 1

HCID 53937337HCID 53937337, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,2,3,9-tetrahydro-9-oxo-pyrrolo[2,1-b]quinazoline-7-carboxylic acid (1.4 g) was reacted with 2-methyl-benzaldehyde (1.65 g) in methanol (50 ml) in the presence of sodium methoxide (1.3 g) under stirring at the reflux temperature for 48 hours. After cooling the reaction mixture was acidified with 37% HCl and the precipitate was filtered and washed with water until neutral: crystallization from chloroform-ethanol gave 1.2 g of 3-(2-methyl-benzylidene)-1,2,3,9-tetrahydro-9-oxo-pyrrolo[2,1-b]quinazoline-7-carboxylic acid, m.p. 285°-287° C., NMR (CF3COOD) δp.p.m.: 2.58 (s) (3H, CH3), 3.66 (m) (2H, C-2 protons), 4.74 (t) (2H, C-1 protons), 7.40-7.85 (m) (4H, phenyl protons), 8.09 (d) (1H, C-5 proton), 8.65 (t) (1H, =CH--), 8.84 (d d) (1H, C-6 proton), 9.30 (d) (1H, C-8 proton).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationthe precipitate was filtered
  3. washwashed with water until neutral:
  4. customcrystallization from chloroform-ethanol

Sources & evidence

ORD record
ord-77c345df7454477b852b52d4f5d07df7
Source dataset
uspto-grants-1984_01
Patent number
US04428952

Reaction notes

Loading…