Potassium Hydroxide → 4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]benzoic acid

HRID 2076424Notes

Reaction equation

HRID 2076424 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([NH:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2.[OH-].[K+]>CO>[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13655816HCID 13655816, compound

Product 1

HCID 21264-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]benzoic acidYield 78.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 25 mL round bottom flask equipped with a reflux condenser was charged with methyl methyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoate 3 (0.200 g, 0.547 mmol), MeOH (10 mL) and KOH (0.122 g, 2.18 mmol). The reaction mixture was stirred for 16 h at reflux, evaporated to dryness and partitioned between EtOAc and H2O. 6N HCl was added until pH became acidic and the organic layer was separated, washed with water, brine, dried with Na2SO4, filtered and concentrated on a rotary evaporator to give 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoic acid 4 as a white solid (0.151 g, 78%).

Workup

  1. customA 25 mL round bottom flask equipped with a reflux condenser
  2. temperatureat reflux
  3. customevaporated to dryness
  4. custompartitioned between EtOAc and H2O
  5. addition6N HCl was added until pH
  6. customthe organic layer was separated
  7. washwashed with water, brine
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-ce56633a077b43f5ac345be186b4e856
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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