Acetic Acid → 2-(2', 4'-Dioxo-1'-methyl-cyclohexyl)-benzyl amine

HRID 53873Notes

Reaction equation

HRID 53873 reaction equation
C1CO[CH:8]2[CH:3]([CH2:4][C:5](=[O:24])[C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18]C(N=[N+]=[N-])=O)([CH3:11])[CH2:7]2)[O:2]1.C(O)(=O)C.C[N:30](C)C=O>>[O:24]=[C:5]1[CH2:4][C:3](=[O:2])[CH2:8][CH2:7][C:6]1([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][NH2:30])[CH3:11]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 867507072-(4'-Ethylenedioxy-1'-methyl-2'-oxocyclohexyl)-phenylacetyl azide

Product 1

HCID 677265002-(2', 4'-Dioxo-1'-methyl-cyclohexyl)-benzyl amine

Conditions

Temperature
100 °C

Procedure

The acyl azide 5 is dissolved in dimethylformamide and heated to 100° C. until nitrogen evolution ceases. The solution is cooled and treated with aqueous acetic acid to form 2-(2', 4'-dioxo-1'-methyl-cyclohexyl)-benzyl amine 6. Diethyl ether is added and the solution is washed successively with saturated sodium bicarbonate solution, water, and saturated salt solution and dried over anhydrous sodium sulfate. The solvent is removed by rotoevaporation to yield 1,2,3,4,4a,5,6,10b-octahydro- 10b-methyl-3-phenanthridinone 7.

Workup

  1. temperatureThe solution is cooled

Sources & evidence

ORD record
ord-93a7c98bbcbc472580c091492ec5d4fa
Source dataset
uspto-grants-1997_04
Patent number
US05621104

Reaction notes

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