Pyridine → HCID 53917626, compound

HRID 2296357Notes

Reaction equation

HRID 2296357 reaction equation
[CH3:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH:4]=[C:5]1[C:9]2=[N:10][C:11]3[CH:12]=[CH:13][C:14]([C:19]([NH2:21])=O)=[CH:15][C:16]=3[C:17](=[O:18])[N:8]2[CH2:7][CH2:6]1.N1C=CC=CC=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>CN(C)C=O>[C:19]([C:14]1[CH:13]=[CH:12][C:11]2[N:10]=[C:9]3[C:5](=[CH:4][C:3]4[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=4[CH3:1])[CH2:6][CH2:7][N:8]3[C:17](=[O:18])[C:16]=2[CH:15]=1)#[N:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 53781214HCID 53781214, compound

Product 1

HCID 53917626HCID 53917626, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3-(2-methyl-benzylidene)-1,2,3,9-tetrahydro-9-oxo-pyrrolo[2,1-b]quinazoline-7-carboxamide (2.7 g) in dimethylformamide (100 ml) containing pyridine (2.6 ml) was reacted with p-toluenesulfonyl chloride (3.1 g) under stirring at 70° C. for 4 hours. After cooling and dilution with water, the precipitate was filtered and washed with water until neutral: crystallization from chloroform-ethanol gave 1.8 g of 7-cyano-3-(2-methyl-benzylidene)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline-9-one, m.p. 234°-236° C., NMR (CDCl3 -DMSO-CF3COOD) δ ppm: 2.50 (s) (3H, --CH3), 3.29 (m) (2H, C-2 protons), 4.28 (t) (2H, C-1 protons), 7.30-7.60 (m) (4H, phenyl protons), 7.89 (m) (2H, C-5 and C-6 protons), 8.16 (d) (1H, C-8 proton), 8.59 (t) (1H, =CH--).

Workup

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

Sources & evidence

ORD record
ord-fa31dca2bcc04e208a62465b204663b2
Source dataset
uspto-grants-1984_01
Patent number
US04428952

Reaction notes

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