Thionyl Chloride → HCID 178487534, compound

HRID 1852155Notes

Reaction equation

HRID 1852155 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]([OH:14])=O)#[N:2].O=S(Cl)[Cl:17]>ClCCl>[Cl:17][C:1]1[C:3]2[C:4](=[CH:5][C:6]([O:9][CH3:10])=[CH:7][CH:8]=2)[CH:11]=[C:12]([OH:14])[N:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 25242077HCID 25242077, compound

Product 1

HCID 178487534HCID 178487534, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

2-(2-cyano-5-methoxyphenyl)acetic acid (3.8 g, 19.88 mmol), and SOCl2 (20 mL, 274 mmol) were stirred in dichloromethane (25 mL) at RT. The suspension became a solution over 8 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 transferred 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-chloro-6-methoxyisoquinolin-3-ol (3.3 g, 70% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 8.10 (d, J=9.6 Hz, 1H), 7.12 (dd, J=9.3, 2.5 Hz, 1H), 6.95 (s, 2H), 3.98 (s, 3H).

Workup

  1. customover 8 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. customtransferred 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-d4d0bd9f7bf54fbd918c3500a5bc8b07
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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