Potassium Hydroxide → HCID 66700930, compound

HRID 1253654Notes

Reaction equation

HRID 1253654 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[C:6]([NH:8][CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([O:21]C)=[O:20])[CH:17]=2)[O:12][CH2:11][CH2:10]1)=[O:7]>C(O)C.O>[Cl:3][C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[C:6]([NH:8][CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=2)[O:12][CH2:11][CH2:10]1)=[O:7]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 66701040HCID 66701040, compound

Product 1

HCID 66700930HCID 66700930, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

KOH (1 mol/1 aq) (2 eq.) was added to a suspension of methyl 4-(2-chlorobenzamido)chroman-6-carboxylate (B-11) (2.227 mmol, 1 eq.) in a mixture of ethanol (13 ml) and water (4.5 ml). The reaction mixture was stirred at room temperature for 16 h. Ethanol was removed in vacuo and the aqueous residue was diluted with diethyl ether (20 ml) and water (20 ml). The phases were separated and the aqueous phase was acidified with 1N HCl to pH 3. The white precipitate was filtered out, washed with aqueous HCl solution and diethyl ether and finally dried in vacuo to obtain the desired product (E-11). Yield: 85%

Workup

  1. customEthanol was removed in vacuo
  2. additionthe aqueous residue was diluted with diethyl ether (20 ml) and water (20 ml)
  3. customThe phases were separated
  4. filtrationThe white precipitate was filtered out
  5. washwashed with aqueous HCl solution and diethyl ether
  6. customfinally dried in vacuo

Sources & evidence

ORD record
ord-b57c28aff64c40ec8cc626faedb4106f
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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