Benzaldehyde → HCID 22395292, compound

HRID 1071837Notes

Reaction equation

HRID 1071837 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[C:14]1(/[CH:13]=[CH:12]/[C:4]2[CH:3]=[C:2]([NH:1][C:21](=[O:23])[CH3:22])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 7918Acetic AnhydrideHCID 811164-Amino-2-methylquinoline

Product 1

HCID 22395292HCID 22395292, compoundYield 64.3%

Procedure

A mixture of 4-aminoquinaldine (2-methyl4-quinolinamine) (3.00 g, 19.0 mmol), benzaldehyde (6.05 g, 5.80 mL, 57.0 mmol) and acetic anhydride (5.82 g, 5.38 mL, 57.0 mmol) was stirred at reflux for 5 h. After cooling, the volume was reduced in vacuo to give a brown oil, which was triturated overnight with diethyl ether. A formed solid was collected by filtration and air-dried to provide the title compound as a yellow solid (3.52 g, 64%). MS (API+): M+1: 289 (100%); 1H NMR (300 MHz, DMSO-d6) d 2.30 (s, 3H), 7.32-7.51 (m, 4H), 7.55-7.65 (m, 1H), 7.70-7.80 (m, 4H), 8.00 (d, J=7.7 Hz, 1H), 8.32 (d, J=8.1 Hz, 1H), 8.38 (s, 1H), 10.24 (s, 1H, exchangeable).

Workup

  1. temperatureat reflux for 5 h
  2. temperatureAfter cooling
  3. customto give a brown oil, which
  4. customwas triturated overnight with diethyl ether
  5. filtrationA formed solid was collected by filtration
  6. customair-dried

Sources & evidence

ORD record
ord-1443b8cea3e64c5a812b39fa45434500
Source dataset
uspto-grants-2005_06
Patent number
US06906193B2

Reaction notes

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