Acetic Acid → HCID 13229174, compound

HRID 1579379Notes

Reaction equation

HRID 1579379 reaction equation
Cl[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[CH2:8][C:7]=2[CH:16]=1.C1N2CN3CN(C2)CN1C3.C(O)(=[O:29])C.Cl>O>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]2[CH2:8][C:7]3[CH:16]=[C:3]([CH:2]=[O:29])[CH:4]=[CH:5][C:6]=3[O:15][C:10]=12

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 12274208HCID 12274208, compound

Product 1

HCID 13229174HCID 13229174, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 52 g of 7-chloromethyl-5H-[1]benzopyrano[2,3-b]pyridine, 63 g of hexamethylenetetramine, 160 ml of water and 160 ml of acetic acid is stirred under reflux for 3 hours. To the reaction mixture is added 80 ml of concentrated hydrochloric acid, and the whole mixture is refluxed for 20 minutes, then diluted with 200 ml of water, and cooled. The crystalline precipitate is filtered off, washed with water, dried, and then recrystallized from dioxane to give 5H-[1]benzopyrano[2,3-b]pyridine-7-carbaldehyde melting at 171°-173°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 dioxane

Sources & evidence

ORD record
ord-b2b560df89df427fb3318e78da2a6ef1
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

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