Ethanol → HCID 13293066, compound

HRID 904817Notes

Reaction equation

HRID 904817 reaction equation
[C:1]([NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O)C>C1COCC1>[CH2:1]([NH:9][C@@H:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11]1[OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 13293063N-(1-Oxo-1,2,3,4-tetrahydronaphthalen-2-yl)benzamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 13293066HCID 13293066, compoundYield 897.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-benzamido-3,4-dihydronaphthalen-1(2H)-one (3.0 g, 1.1 mmole) in THF (150 ml) was added dropwise to a suspension of LiAlH4 (2.0 g) in THF (50 ml). The reaction was heated at reflux for 2 hr and then cooled to room temperature. Enough ethanol was added to destroy excess LiAlH4 followed by 150 ml of Rochell's salt solution (20%). The resulting mixture was extracted with ethyl acetate, the ethyl acetate layer was washed with brine and dried over Na2SO4. Evaporation of the solvent afforded 2.5 g (88%) of the product, m.p. 110°-114° C. After recrystallization from cyclohexane it had m.p. 112°-115° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hr
  3. customto destroy excess LiAlH4
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washthe ethyl acetate layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f43725a652944e8fa58691821f871460
Source dataset
uspto-grants-1983_12
Patent number
US04420480

Reaction notes

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