Phosphorus oxychloride → HCID 86761207, compound

HRID 1170878Notes

Reaction equation

HRID 1170878 reaction equation
O[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]([OH:20])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:2]1[C:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18](=[O:20])[C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178524026HCID 178524026, compound

Product 1

HCID 86761207HCID 86761207, compoundYield 87%

Conditions

Temperature
150 °C

Procedure

2.65 g (10 mmol) of 2-hydroxy-3-phenylquinoline-4-carboxylic acid (3a) was added into POCl3 (30 mL) and heated at 150° C. for 48 hrs (TLC monitoring). After cooling, the mixture was poured into ice-water (150 mL) to result in precipitation, followed by filtration. The resultant filter cake was poured into 5% NaHCO3(aq) (200 mL) with vigorous stirring for 1 hr, washed with H2O, and dried to give a brown solid, which was recrystallized with EtOH to give the title compound 4a as a red solid (2.31 g, 87% yield).

Workup

  1. temperatureAfter cooling
  2. customto result in precipitation
  3. filtrationfollowed by filtration
  4. filtrationThe resultant filter cake
  5. additionwas poured into 5% NaHCO3(aq) (200 mL)
  6. washwashed with H2O
  7. customdried
  8. customto give a brown solid, which
  9. customwas recrystallized with EtOH

Sources & evidence

ORD record
ord-8f96be5e1ea84b72a5d0e980fea5667d
Source dataset
uspto-grants-2010_11
Patent number
US07829567B2

Reaction notes

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