Sodium Carbonate → HCID 22693553, compound

HRID 408649Notes

Reaction equation

HRID 408649 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH3:19])[CH:13]=[C:12]2O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].P(Cl)(Cl)([Cl:29])=O>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH3:19])[CH:13]=[C:12]2[Cl:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178428855HCID 178428855, compound

Product 1

HCID 22693553HCID 22693553, compound

Procedure

6-Benzyloxy-4-hydroxy-2-methylquinoline (2.6 g; see step (ii) above) in phosphorus oxychloride (40 mL) was heated at reflux for 3.5 hours. The mixture was then added carefully to ice/water and solid sodium carbonate added until the solution reached pH 8.0. The mixture was extracted with ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated. The resulting solid was triturated with diethyl ether to give the title compound (6.4 g) as a white solid.

Workup

  1. temperatureat reflux for 3.5 hours
  2. additionadded until the solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-2ad0d1abf48248a8b7ccdb70c7eb4fbb
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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