Hydrochloric Acid → 8-(2,6-Dichloro-3-hydroxybenzyloxy)-2-methylquinoline

HRID 1604562Notes

Reaction equation

HRID 1604562 reaction equation
[Cl:1][C:2]1[C:20]([O:21]COC)=[CH:19][CH:18]=[C:17]([Cl:25])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.Cl>CO>[Cl:1][C:2]1[C:20]([OH:21])=[CH:19][CH:18]=[C:17]([Cl:25])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 196033098-[2,6-Dichloro-3-(methoxymethoxy)benzyloxy]-2-methylquinoline

Product 1

HCID 196033608-(2,6-Dichloro-3-hydroxybenzyloxy)-2-methylquinolineYield 52.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-[2,6-dichloro-3-(methoxymethoxy)benzyloxy]-2-methylquinoline (1.57 g) in methanol was dropwise added conc. hydrochloric acid (2.7 ml) at 0° C., and the mixture was stirred for 5 minutes. The solvent was removed, and water was added thereto. The mixture was neutralized with saturated sodium bicarbonate solution, and the resulting participates were collected by filtration to give 8-(2,6-dichloro-3-hydroxybenzyloxy)-2-methylquinoline (734 mg) as a solid.

Workup

  1. customat 0° C.
  2. customThe solvent was removed
  3. additionwater was added
  4. filtrationthe resulting participates were collected by filtration

Sources & evidence

ORD record
ord-bee8461d7e4f4fbe85b6b04ff8ec518e
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

Loading…