Hydrochloric Acid → HCID 12274208, compound

HRID 1579440Notes

Reaction equation

HRID 1579440 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[CH2:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:3]=12.[CH2:16]=O.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:1][CH2:16][C:14]1[CH:13]=[CH:12][C:10]2[O:11][C:3]3=[N:2][CH:7]=[CH:6][CH:5]=[C:4]3[CH2:8][C:9]=2[CH:15]=1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 712Formaldehyde2×HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 122742075H-[1]benzopyrano[2,3-b]pyridine

Product 1

HCID 12274208HCID 12274208, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydrogen chloride gas is passed through a mixture of 10 g of 5H-[1]-benzopyrano[2,3-b]pyridine, 1.4 g of paraformaldehyde, 110 ml of concentrated sulfuric acid and 22 ml of concentrated hydrochloric acid at 80°C for 12 hours, while 2 g of paraformaldehyde is added in several portions to the reaction mixture. The reaction mixture is poured into water, and the whole mixture is neutralized with sodium carbonate, and extracted with a large amount of chloroform. The chloroform layer is dried, concentrated to 30 ml, and cooled. The resulting crystalline precipitate is filtered off, and recrystallized from chloroform to give 7-chloromethyl-5H-[1]benzopyrano[2,3-b]pyridine melting at 172°-174°C.

Workup

  1. additionis added in several portions to the reaction mixture
  2. extractionextracted with a large amount of chloroform
  3. dry with materialThe chloroform layer is dried
  4. concentrationconcentrated to 30 ml
  5. temperaturecooled
  6. filtrationThe resulting crystalline precipitate is filtered off
  7. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-8f3e8175e73149e2b25276b24b4c9133
Source dataset
uspto-grants-1976_01
Patent number
US03931205

Reaction notes

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