Ethyl Acetate → 7-Hydroxycarbostyril

HRID 1655023Notes

Reaction equation

HRID 1655023 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](Cl)(=[O:18])[CH:10]=[CH:11]C1C=CC=CC=1.CCOC(C)=O>C(Cl)Cl.N1C=CC=CC=1>[OH:8][C:4]1[CH:3]=[C:2]2[C:7]([CH:11]=[CH:10][C:9](=[O:18])[NH:1]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 115683-AminophenolHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 109757877-Hydroxycarbostyril

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-aminophenol (1 g) in CH2Cl2 (25 mL) and pyridine (1 mL) at 5° C. was added dropwise a solution of cinnamoyl chloride (1.53 g) in CH2Cl2 (10 mL). The mixture was warmed to r.t. over 1 hr, and then EtOAc (150 mL) was added. The organics were washed with H2O, 1N, HCl, saturated aq. NaHCO3 and H2O, dried (MgSO4) and concentrated. To the residue was added AlCl3 (6.38 g) and the mixture heated at 180° C. for 5 min. and then at 115°-120° C. for 2 hr. To the mixture was added ice and then H2O. The solid that formed was collected by filtration, washed with 2N HCl and H2O (3×). The resulting solid was triturated in EtOAc to provide the title compound.

Workup

  1. washThe organics were washed with H2O, 1N, HCl, saturated aq. NaHCO3 and H2O
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. additionTo the residue was added AlCl3 (6.38 g)
  5. temperaturethe mixture heated at 180° C. for 5 min.
  6. additionTo the mixture was added ice
  7. customThe solid that formed
  8. filtrationwas collected by filtration
  9. washwashed with 2N HCl and H2O (3×)
  10. customThe resulting solid was triturated in EtOAc

Sources & evidence

ORD record
ord-84bcab8d5fb54118a5f5807ebd975af0
Source dataset
uspto-grants-1995_04
Patent number
US05410054

Reaction notes

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