Ethyl acetate hexane → 2-Ethylamino-4-trifluoromethyl-benzaldehyde

HRID 1042464Notes

Reaction equation

HRID 1042464 reaction equation
[CH2:1]([NH:3][C:4]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:5]=1[C:6](N(OC)C)=[O:7])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].CCCCCC.C(OC(=O)C)C>C1COCC1>[CH2:1]([NH:3][C:4]1[CH:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:13]=[CH:12][C:5]=1[CH:6]=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydrideHCID 866499602-ethylamino-N-methoxy-N-methyl-4-trifluoromethyl-benzamide

Product 1

HCID 866499612-Ethylamino-4-trifluoromethyl-benzaldehydeYield 29.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Ethylamino-N-methoxy-N-methyl-4-trifluoromethyl-benzamide (95 mg, 0.343 mmol) was reacted with LAH in THF at −40° C. for 1.5 hrs as described above to yield title compound (22 mg, 29%) after column chromatography (hexane/ethylacetate=20/1).

Sources & evidence

ORD record
ord-94292db96b1244739583925b718f0f3e
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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