Sodium Hydroxide → 2-Formyl-5,6-dihydro-8-methoxy-9-(1-methylethoxy)-1-(2-thienyl)pyrrolo[2,1-a]isoquinoline-3-carboxylic acid

HRID 1971711Notes

Reaction equation

HRID 1971711 reaction equation
[CH:1]([C:3]1[C:4]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)=[C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:19][CH3:20])=[C:12]([O:15][CH:16]([CH3:18])[CH3:17])[CH:13]=3)[CH2:8][CH2:7][N:6]2[C:21]=1[C:22]([O:24]CC)=[O:23])=[O:2].[OH-].[Na+]>C(O)C>[CH:1]([C:3]1[C:4]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)=[C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:19][CH3:20])=[C:12]([O:15][CH:16]([CH3:17])[CH3:18])[CH:13]=3)[CH2:8][CH2:7][N:6]2[C:21]=1[C:22]([OH:24])=[O:23])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58124902HCID 58124902, compound

Product 1

HCID 581249292-Formyl-5,6-dihydro-8-methoxy-9-(1-methylethoxy)-1-(2-thienyl)pyrrolo[2,1-a]isoquinoline-3-carboxylic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 815 mg of 15c in 40 ml of ethanol was mixed with 18 ml of 2N NaOH. The mixture was stirred for 1 h at 60° C. The mixture was cooled and concentrated to half its original volume and diluted with 30 ml of water, acidified with 0.5N NaOH and extracted with ethyl acetate. The organic extract was washed with water, dried and concentrated to provide 750 mg of 15d as an amorphous material, which was used without further purification in the next step.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated to half its original volume
  3. additiondiluted with 30 ml of water
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d9bdd317f1b64a76854d9b92b6a454ac
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

Loading…