Thionyl Chloride → HCID 178515367, compound

HRID 1852133Notes

Reaction equation

HRID 1852133 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[N:9])[C:3]=1[CH2:10][C:11]([OH:13])=O.O=S(Cl)[Cl:16]>ClCCl>[Cl:16][C:8]1[C:4]2[C:3](=[C:2]([Cl:1])[CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:11]([OH:13])[N:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68147289Benzeneacetic acid, 2-chloro-6-cyano-

Product 1

HCID 178515367HCID 178515367, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

2-(2-chloro-6-cyanophenyl)acetic acid (10.5 g, 53.7 mmol) and SOCl2 (20 mL, 274 mmol) were stirred in dichloromethane (25 mL) at RT. The suspension became a solution over 4 h. The reaction was stirred overnight. The volitile organics were removed under vacuum and the residue was taken up in DCM and filtered. The filtrate was concentrated and then dissolved in 4 N HCl dioxane (30 mL) and transfered to a sealed vessel and heated to 60° C. for 3 h. The reaction was cooled and the solid was collected, washed with dioxane, and dried under vacuum to give the product 1,5-dichloroisoquinolin-3-ol (8 g, 69.6% yield) as a solid 1H NMR (400 MHz, DMSO-d6) δ 11.66 (s, 1H), 8.11 (dt, J=8.6, 1.0 Hz, 1H), 7.90 (dd, J=7.6, 1.0 Hz, 1H), 7.46 (dd, J=8.6, 7.6 Hz, 1H), 7.11 (d, J=1.0 Hz, 1H). MS: MS m/z 214.08(M++1).

Workup

  1. customover 4 h
  2. customThe volitile organics were removed under vacuum
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. dissolutiondissolved in 4 N HCl dioxane (30 mL)
  6. customtransfered to a sealed vessel
  7. temperatureThe reaction was cooled
  8. customthe solid was collected
  9. washwashed with dioxane
  10. customdried under vacuum

Sources & evidence

ORD record
ord-24592308b3ee4609905d3412d1097fd5
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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