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Sodium Hydroxide → 7-(4-Carboxy-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

HRID 1876288
Notes
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Reaction equation

HRID 1876288 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]([N:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][C:17]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([O:32]CC)=[O:31])=[CH:26][CH:25]=3)=[CH:18][CH:19]=2)[CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([O:10][C:11]([N:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][C:17]([O:23][C:24]3[CH:25]=[CH:26][C:27]([C:30]([OH:32])=[O:31])=[CH:28][CH:29]=3)=[CH:18][CH:19]=2)[CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 584938427-(4-Ethoxycarbonyl-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

Product 1

HCID 584938387-(4-Carboxy-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

Sodium hydroxide (0.73 g dissolved in 25 mL water) is added to a solution of 7-(4-ethoxycarbonyl-phenoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (3.00 g) in ethanol (100 mL). The resulting suspension is stirred at 45° C. overnight. The solution is concentrated and the aqueous residue is adjusted to pH value 2-3 using 1 M hydrochloric acid. Then dichloromethane is added and the mixture is stirred for 10 min. The organic phase is separated and the aqueous phase is extracted with dichloromethane twice. The combined organic phases are dried (Na2SO4) and concentrated. The residue is purified by chromatography on silica gel (petrol ether/ethyl acetate/acetic acid 50:50:0.5) to furnish the title compound as an oil.

Workup

  1. concentrationThe solution is concentrated
  2. additionThen dichloromethane is added
  3. stirringthe mixture is stirred for 10 min
  4. customThe organic phase is separated
  5. extractionthe aqueous phase is extracted with dichloromethane twice
  6. dry with materialThe combined organic phases are dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue is purified by chromatography on silica gel (petrol ether/ethyl acetate/acetic acid 50:50:0.5)

Sources & evidence

ORD record
ord-acd3e34054c044a5a537d4ddc82ee019
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08309597B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes