Thionyl Chloride → HCID 54101367, compound

HRID 1085434Notes

Reaction equation

HRID 1085434 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([OH:16])=O)[N:2]=1.S(Cl)(Cl)=O>CN(C)C=O>[CH2:1]([N:2]([CH2:3][CH3:4])[C:14]([C:3]1[N:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3)=[O:16])[CH3:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1732629H-Pyrido(3,4-b)indole-3-carboxylic acid

Product 1

HCID 54101367HCID 54101367, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2 g of β-carbolin-3-carboxylic acid, 20 ml of thionyl chloride and 2 ml of dimethylformamide is boiled under reflux for 1 hour. The excess thionyl chloride is removed by distillation under reduced pressure. 20 ml of diethylamine is added under cooling to a suspension of the residue in 20 ml of triethylamine and the mixture is concentrated under reduced pressure. The residue is treated with aqueous ammonia (pH 8.5) and the mixture thus obtained is extracted with chloroform (6×25 ml). The extract is washed with water (2×25 ml), dried (K2CO3), decolorized with a small amount of charcoal and filtered. The filtrate is evaporated to dryness and the residue is kept at 60° C. overnight. The solid (1.56 g; 62%) is recrystallized from toluene to form β-carbolin-3-carboxylic acid diethylamide having a melting point of 170.0° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe excess thionyl chloride is removed by distillation under reduced pressure
  3. addition20 ml of diethylamine is added
  4. temperatureunder cooling to a suspension of the residue in 20 ml of triethylamine
  5. concentrationthe mixture is concentrated under reduced pressure
  6. additionThe residue is treated with aqueous ammonia (pH 8.5)
  7. customthe mixture thus obtained
  8. extractionis extracted with chloroform (6×25 ml)
  9. washThe extract is washed with water (2×25 ml)
  10. dry with materialdried (K2CO3)
  11. filtrationfiltered
  12. customThe filtrate is evaporated to dryness
  13. customThe solid (1.56 g; 62%) is recrystallized from toluene

Sources & evidence

ORD record
ord-b2db1071bec4472c96bb76042f5950f3
Source dataset
uspto-grants-1991_04
Patent number
US05010077

Reaction notes

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