Ammonia → HCID 19707385, compound

HRID 1741894Notes

Reaction equation

HRID 1741894 reaction equation
[C:1]1([CH2:7][C:8](O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([NH2:15])[CH2:12][CH2:13][CH3:14].N.[CH2:17]1[CH:26]2[CH:21]([CH2:22][CH2:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=32)[NH:20][C:19](=[O:31])[CH2:18]1>C(O)CO.C(COC)OC>[CH2:21]([N:20]1[C:11]2[C:7]([CH3:8])([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=3[CH2:13][CH:12]=2)[CH2:17][CH2:18][C:19]1=[O:31])[CH2:26][CH2:25][CH3:27].[CH2:11]([N:15]1[C@@H:21]2[C@:26]([CH3:1])([C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[CH2:23][CH2:22]2)[CH2:17][CH2:18][C:19]1=[O:31])[CH2:12][CH2:13][CH3:14]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 999Phenylacetic AcidHCID 8007ButylamineHCID 19707357HCID 19707357, compound

Product 2

HCID 19707385HCID 19707385, compoundHCID 53898870trans-4-n-Butyl-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

By following the procedures described in Example 40, Steps A, B, C, D, E and F using phenylacetic acid as the starting material and in Step F using n-butylamine rather than ammonia and dimethoxyethane rather than ethylene glycol, the compound 4-n-butyl-10b-methyl-1,2,3,4,6,10b-hexahydrobenzo[f]quinolin-3-one was prepared. This hexahydrobenzo[f]quinolin-3-one was hydrogenated by following the procedures described Example 22 except that the reaction was carried out at 60° C. over 7 hours and worked up according to the procedures described in Example 42 to afford 61 mg of the title compound as a colorless oil.

Sources & evidence

ORD record
ord-d0418d8838984a9a97a2c66e2858eb34
Source dataset
uspto-grants-1994_08
Patent number
US05334767

Reaction notes

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