Sodium Hydroxide → HCID 58289674, compound

HRID 1422534Notes

Reaction equation

HRID 1422534 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12](O)[C:11]2[C:6](=[C:7]([CH3:17])[C:8]([O:15][CH3:16])=[CH:9][CH:10]=2)[N:5]=1)[CH3:2].[OH-].[Na+].O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:12]1[C:11]2[C:6](=[C:7]([CH3:17])[C:8]([O:15][CH3:16])=[CH:9][CH:10]=2)[N:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:13]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178467004HCID 178467004, compound

Product 1

HCID 58289674HCID 58289674, compound

Conditions

Temperature
85 °C

Procedure

2-Ethoxy-7-methoxy-8-methyl-quinolin-4-ol (1.0 g, 4.3 mmol) was dissolved in POCl3 (21 mL) under a nitrogen atmosphere. The reaction was heated to 85° C. for 1 h. The reaction was cooled to 0° C. and ice was added slowly. After 30 min, pH was adjusted to 6 with 1N NaOH(aq). The solution was extracted with ethyl acetate (2×50 mL). The organic layers were dried with sodium sulfate, filtered and were concentrated. 4-Chloro-2-ethoxy-7-methoxy-8-methyl-quinoline (875 mg, 81%) was purified by silica gel chromatography to afford a white solid.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. additionice was added slowly
  3. extractionThe solution was extracted with ethyl acetate (2×50 mL)
  4. dry with materialThe organic layers were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationwere concentrated
  7. custom4-Chloro-2-ethoxy-7-methoxy-8-methyl-quinoline (875 mg, 81%) was purified by silica gel chromatography
  8. customto afford a white solid

Sources & evidence

ORD record
ord-6876ed12a1a048fe809373d3359a05ff
Source dataset
uspto-grants-2015_01
Patent number
US08927484B2

Reaction notes

Loading…