Ammonia → 8-Acetamido-2-tetralone

HRID 863506Notes

Reaction equation

HRID 863506 reaction equation
N.[C:2]([NH:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([O:16]C)[CH:12]=[CH:11]2)(=[O:4])[CH3:3].C(O)(C)(C)C.[Na].[Cl-].[Na+]>C(O)(=O)C.C1COCC1>[C:2]([NH:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)(=[O:4])[CH3:3]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 6386tert-ButanolHCID 5360545SodiumHCID 11447230N-(7-methoxynaphthalen-1-yl)acetamide

Product 1

HCID 134241118-Acetamido-2-tetraloneYield 42.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonia (300 mL) was condensed in a flask containing 8-Acetamido-2-methoxynaphthalene (24.5 g, 115 mmol), t-butyl alcohol (34 g, 0.46 mol) and THF (300 mL). Sodium (8 g, 0.35 mol) was added in portions and the mixture was stirred for 3 h and allowed to warm to room temperature. The mixture was poured onto ice and saturated sodium chloride, and then extracted with THF (3×). The combined organic layers were washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to give a dark solid. The residue was dissolved in 50% acetic acid and heated at 95° C. for 18 h. After evaporation, the residue was suspended in dimethyl ether and collected by filtration and dried. The filtrate was purified by silica gel chromatography (3:2 EtOAc:hexane) and combined with the other product to give a tan solid (10 g).

Workup

  1. customcondensed in a flask
  2. extractionextracted with THF (3×)
  3. washThe combined organic layers were washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a dark solid
  8. temperatureheated at 95° C. for 18 h
  9. customAfter evaporation
  10. filtrationcollected by filtration
  11. customdried
  12. customThe filtrate was purified by silica gel chromatography (3:2 EtOAc:hexane)

Sources & evidence

ORD record
ord-9067906bf602496ea95b8c9492f74b14
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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