Water → HCID 59314138, compound

HRID 1047719Notes

Reaction equation

HRID 1047719 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:27]=2[NH:26][CH2:25][CH2:24][CH2:23]3)=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[NH:26]1[C:27]2[C:22](=[CH:21][CH:20]=[CH:19][C:18]=2[C:16]([NH:15][C:6]2([C:4]([OH:5])=[O:3])[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7]2)=[O:17])[CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314175HCID 59314175, compound

Product 1

HCID 59314138HCID 59314138, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-[(1,2,3,4-tetrahydro-quinoline-8-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (63) (259 mg, 0.71 mmol) and KOH (1 g, 17.9 mmol) is dissolved in EtOH (15 mL) and water (1 mL) under a water bath. The water bath is removed when KOH is completely dissolved and the resulting reaction solution is stirred at RT for 8 h. After concentration in vacuo, the residue is dissolved in water (30 mL) and acidified with conc. HCl dropwise until precipitate falls out of the water. After the filtration, the solid is washed by water and collected. The filtrate is acidified with conc. HCl carefully again to see if more precipitate comes out or not. The combined solid is dried in vacuo to give a pure product (64) as a yellow solid (205 mg, 86%).

Workup

  1. customThe water bath is removed when KOH
  2. dissolutionis completely dissolved
  3. customthe resulting reaction solution
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue is dissolved in water (30 mL)
  6. filtrationAfter the filtration
  7. washthe solid is washed by water
  8. customcollected
  9. customThe combined solid is dried in vacuo

Sources & evidence

ORD record
ord-4f66bacf8c7a4b5b9612caedc1c9cc0c
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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