Acetic Acid → HCID 12898475, compound

HRID 1579376Notes

Reaction equation

HRID 1579376 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:15][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[O:16])[C:7]=2[CH:17]=1.C1N2CN3CN(C2)CN1C3.C(O)(=[O:30])C.Cl>O>[O:16]=[C:8]1[C:9]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[O:15][C:6]2[CH:5]=[CH:4][C:3]([CH:2]=[O:30])=[CH:17][C:7]1=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 122742035H-[1]Benzopyrano[2,3-b]pyridin-5-one, 7-(bromomethyl)-

Product 1

HCID 12898475HCID 12898475, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 50 g of 7-bromomethyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine, 48.4 g of hexamethylenetetramine, 167 ml of water and 167 ml of acetic acid is stirred under reflux for 3 hours. To the reaction mixture is added 100 ml of concentrated hydrochloric acid, and the whole mixture is refluxed for 20 minutes. The reaction mixture is diluted with 200 ml of water, and cooled. The crystalline precipitate is filtered off, washed with water, dried, and then recrystallized from dimethylformamide to give 5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-7-carbaldehyde melting at 233-235°C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperaturethe whole mixture is refluxed for 20 minutes
  3. temperaturecooled
  4. filtrationThe crystalline precipitate is filtered off
  5. washwashed with water
  6. customdried
  7. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-0f4bfea9a1524446bb412c55e466c363
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

Loading…