Sodium Hydroxide → [4-(4-Benzoylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid

HRID 1468462Notes

Reaction equation

HRID 1468462 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:31])[CH:11]=2)[CH:6]=1.[OH-].[Na+]>C(O)C.C1COCC1>[C:23]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([Cl:31])[CH:11]=3)[CH:6]=[C:5]([CH2:4][C:3]([OH:32])=[O:2])[C:14]=2[CH3:15])=[CH:21][CH:20]=1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86695035[4-(4-Benzoylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

Product 1

HCID 71711714[4-(4-Benzoylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acidYield 92.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(4-benzoylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (130 mg, 0.29 mmol) in ethanol (3 mL) and THF (3 mL) was added a solution of sodium hydroxide (879 uL, 1.0 N) at room temperature. The resulting clear solution was stirred overnight. The solvents were removed under vacuum and the residue was diluted with water (10 mL), acidified with 1.0 N hydrochloric acid, and extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with brine solution (20 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent under vacuum afforded (115 mg, 91.3%) [4-(4-benzoylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.51 (br. s, 1 H), 10.46 (s, 1 H), 7.91-8.04 (m, 5 H), 7.86 (s, 1 H), 7.51-7.68 (m, 3 H), 7.47 (dd, J=8.8, 1.8 Hz, 1 H), 7.23 (d, J=8.5 Hz, 2 H), 7.18 (d, J=1.8 Hz, 1 H), 3.85 (s, 2 H), 2.12 (s, 3 H). HRMS calcd. for C26H21ClNO3 [(M+H)+] 430.1205, obsd. 430.1205.

Workup

  1. customThe solvents were removed under vacuum
  2. additionthe residue was diluted with water (10 mL)
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. washThe combined organic extracts were washed with brine solution (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration of the drying agent and concentration of the solvent under vacuum

Sources & evidence

ORD record
ord-f5db9b99cc3c4ae29c61e88adfed7e6f
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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