Benzaldehyde → HCID 54221010, compound

HRID 2296355Notes

Reaction equation

HRID 2296355 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8](=[O:17])[N:9]3[CH2:16][CH2:15][CH2:14][C:10]3=[N:11][C:12]=2[CH:13]=1)([O-:3])=[O:2].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C[O-].[Na+]>CO>[CH:18](=[C:14]1[C:10]2=[N:11][C:12]3[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=3[C:8](=[O:17])[N:9]2[CH2:16][CH2:15]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 10942334Sodium MethoxideHCID 12344017HCID 12344017, compound

Product 1

HCID 54221010HCID 54221010, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-nitro-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline-9-one, m.p. 196°-197° C. (3.7 g), prepared according to the Example 2, was reacted with benzaldehyde (2 g) in methanol (100 ml) in the presence of sodium methoxide (1.74 g) under stirring at room temperature for 16 hours and then at 60° C. for 4 hours. After concentration in vacuo of the suspension, the precipitate was filtered and washed with water until neutral: crystallization from CH2Cl2 -methanol gave 3-benzylidene-6-nitro-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline-9-one, m.p. 255°-257° C. (3.5 g), which was reacted with SnCl2.2H2O (25 g) in 37% HCl (15 ml) and acetic acid (45 ml) under stirring at 60° C. for 3 hours. After cooling the precipitate was filtered and washed with water and then suspended under stirring in 2.5% aqueous NaHCO3 : the product was filtered, washed with water until neutral and then crystallized from ethanol to give 1.6 g of 6-amino-3-benzylidene-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline-9-one, m.p. 268°-270° C., NMR (DMSO-d6) δppm: 3.23 (bt) (2H, C-2 protons), 4.11 (t) (2H, C-1 protons), 6.07 (bs) (2H, --NH2), 6.73 (m), (2H, C-5 and C-7 protons), 7.33-7.76 (m) (5H, phenyl protons), 7.68 (bs) (1H, =CH--), 7.83 (d) (1H, C-8 proton).

Workup

  1. waitat 60° C. for 4 hours
  2. concentrationAfter concentration in vacuo of the suspension
  3. filtrationthe precipitate was filtered
  4. washwashed with water until neutral:
  5. customcrystallization from CH2Cl2 -methanol

Sources & evidence

ORD record
ord-b3a318a6b42442e99fd010ce0070911e
Source dataset
uspto-grants-1984_01
Patent number
US04428952

Reaction notes

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