Methanol → HCID 68821594, compound

HRID 1819749Notes

Reaction equation

HRID 1819749 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH:11][NH2:12])=[N:3][CH:2]=1.[C:13]1([CH3:21])[C:14](C=O)=[CH:15][CH:16]=[CH:17][CH:18]=1.[CH3:22]O>>[CH3:21][C:13]1[CH:18]=[CH:17][C:16]([CH:22]=[N:12][NH:11][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][N:3]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 107222-MethylbenzaldehydeHCID 633434-Hydrazinoquinazoline

Product 1

HCID 68821594HCID 68821594, compoundYield 87%

Procedure

A solution of quinazolin-4-yl-hydrazine (Gewald et al., J. Prakt. Chem./Chem.-Ztg. 1996, 338, 206-213) (265 mg, 1.65 mmol) was refluxed with tolualdehyde (400 μl, 3.39 mmol) in methanol for 1 hour. The solvent was evaporated and the resulting solid was triturated with water and filtered to give a yellow powder in 87% yield: mp 211-214° C.; 1H-NMR (DMSO-d6) 2.37 (s, 3H), 7.29 (d, 2H), 7.47 (dt, 2H), 7.67 (t, 1H), 7.88 (d, 3H), 8.20 (m, 1H), 8.51 (s, 1H), 11.65 (s, 1H); HR-MS (EI) m/z 262.1223 (M+).

Workup

  1. customThe solvent was evaporated
  2. customthe resulting solid was triturated with water
  3. filtrationfiltered
  4. customto give a yellow powder in 87% yield

Sources & evidence

ORD record
ord-958c82f357b247a4832b75df626a495f
Source dataset
uspto-grants-2009_10
Patent number
US07601846B2

Reaction notes

Loading…