2-Methoxybenzaldehyde → HCID 56612712, compound

HRID 1247943Notes

Reaction equation

HRID 1247943 reaction equation
[O:1]=[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]2[CH:12]=[CH:13][C:14]([C:16]([O:18]C)=[O:17])=[CH:15][N:3]12.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=O>C(O)(C)(C)C>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=[C:7]1[C:6]2[N:5]=[C:4]3[CH:12]=[CH:13][C:14]([C:16]([OH:18])=[O:17])=[CH:15][N:3]3[C:2](=[O:1])[C:11]=2[CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 86582-MethoxybenzaldehydeHCID 13251421HCID 13251421, compound

Product 1

HCID 56612712HCID 56612712, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1,2,3,4-tetrahydro-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid, methyl ester (2.5 g) was reacted with 2-methoxy-benzaldehyde (2.6 g) in tert.butanol (75 ml) in the presence of potassium tert.butylate (4.3 g) under stirring at reflux temperature for 8 hours. After cooling the solution was concentrated in vacuo to a small volume and the precipitate was filtered and washed with little methanol and then dissolved in water containing NaHCO3 : the solution was acidified with 23% HCl to pH=4 and the precipitate was filtered and washed with water until neutral. Crystallization from acetone gave 1.1 g of 4-(2-methoxy-benzylidene)-1,2,3,4-tetrahydro-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid, m.p. 300° C. (dec.), N.M.R. (CDCl3 -CF3COOD) δp.p.m.: 1.93 (m) (2H,C-2 protons), 2.84 (m) (4H, C-1 and C-3 protons), 3.81 (s) (3H, --OCH3), 6.80-7.50 (m) (4H, phenyl protons), 7.70 (bs) (1H, =CH--), 8.17 (d) (1H, C-6 proton), 8.69 (dd) (1H, C-7 proton), 9.73 (d) (1H,C-9 proton).

Workup

  1. temperatureat reflux temperature for 8 hours
  2. temperatureAfter cooling the solution
  3. concentrationwas concentrated in vacuo to a small volume
  4. filtrationthe precipitate was filtered
  5. washwashed with little methanol
  6. dissolutiondissolved in water
  7. additioncontaining NaHCO3
  8. filtrationthe precipitate was filtered
  9. washwashed with water until neutral
  10. customCrystallization from acetone

Sources & evidence

ORD record
ord-2ef5dcee788d48629651d422ecd07ce9
Source dataset
uspto-grants-1985_06
Patent number
US04521419

Reaction notes

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