Ethanol → HCID 9927310, compound

HRID 2290130Notes

Reaction equation

HRID 2290130 reaction equation
C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH3:25])[C:12]2[CH:13]=[C:14]([CH2:23]C)[C:15]3[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]=3[CH:22]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+].[CH2:29](O)C>>[CH2:25]([N:11]([C:12]1[CH:13]=[C:14]([CH3:23])[C:15]2[O:19][CH2:18][C:17]([CH3:20])([CH3:21])[C:16]=2[CH:22]=1)[C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:3])=[O:26])=[CH:10][CH:9]=1)[CH3:29]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 15454089HCID 15454089, compound2×

Product 1

HCID 9927310HCID 9927310, compoundYield 80%

Procedure

A solution of 4-[methyl-(7-ethyl-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 21, 0.095 g, 0.27 mmol) in 10 mL of ethanol was treated with 2 mL (10 mmol) of 5M sodium hydroxide solution and the reaction mixture was stirred overnight at room temperature, and at 55° C. for 2 hours. The volatiles were removed by distillation in vacuo and the residue was neutralized with dilute hydrochloric acid, and extracted with ethyl acetate. The organic extract was washed with brine and dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound (0.070 g, 80%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.92 (d, 2H, J=9.0 Hz), 6.83 (d, 1H, J=2.1 Hz), 6.80 (d, 1H, J=2.1 Hz), 6.65 (d, 2H, J=9.0 Hz), 4.30 (s, 2H), 3.34 (s, 3H), 2.64 (q, 2H, J=7.6 Hz), 1.35(s, 6H), 1.23 (t, 3H, J=7.6 Hz).

Workup

  1. waitat 55° C. for 2 hours
  2. customThe volatiles were removed by distillation in vacuo
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-c8243fc253734af0ae52550900baf589
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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