Water → HCID 19008956, compound

HRID 1742427Notes

Reaction equation

HRID 1742427 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([NH:19]C(=O)C)=[CH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].O>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([NH2:19])=[CH:14][CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 19008945HCID 19008945, compound

Product 1

HCID 19008956HCID 19008956, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(6-benzyloxy-naphthalen-1-yl)-acetamide (5.0 grams, 17 mmol) and potassium hydroxide (2.88 grams, 51 mmol) in EtOH (35 mL)/H2O (25 mL) was heated at 93° C. for 17 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuo. The residue was diluted with saturated aqueous NaCl (25 mL) and extracted with EtOAc (5×100 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The crude residue was chromatographed on SiO2 -gel using 30% ethyl acetate/hexanes. 1H NMR (250 MHz, CDCl3): d 7.78 (d, 1 H), 7.50 (s, 1 H), 7.38 (m, 3 H), 7.20 (m, 4 H), 6.67 (d, 1 H), 5.18 (s, 2 H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with saturated aqueous NaCl (25 mL)
  3. extractionextracted with EtOAc (5×100 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was chromatographed on SiO2

Sources & evidence

ORD record
ord-e6677b773e1446779f79e9fda7eb1464
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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