Thionyl Chloride → HCID 20063347, compound

HRID 1084448Notes

Reaction equation

HRID 1084448 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]([CH:19]([CH3:21])[CH3:20])[C:9]=2[C:22]([OH:24])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:27])=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]([CH:19]([CH3:21])[CH3:20])[C:9]=2[C:22]([Cl:27])=[O:24])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 20063337HCID 20063337, compound

Product 1

HCID 20063347HCID 20063347, compound

Procedure

A mixture of 4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid (4.9 g) and thionyl chloride (50 ml) was heated at reflux for 90 minutes. The excess thionyl chloride was then removed by evaporation in vacuo (15 mmHg/40° C.) followed three times by treatment with dichloromethane and evaporation in vacuo, to give 4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinoline-3-carbonyl chloride (4.35 g) in the form of a white solid, m.p.132°-134° C. [Elemental analysis: C,66.4; H,4.4; N,4.04; Cl,10.3%; calculated: C,66.4; H,4.40; N,4.08; Cl,10.31%].

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 90 minutes
  3. customThe excess thionyl chloride was then removed by evaporation in vacuo (15 mmHg/40° C.)
  4. customwith dichloromethane and evaporation in vacuo

Sources & evidence

ORD record
ord-d881c026d49a428f9a9c4e9930a8dbdd
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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