Ammonia → HCID 10106832, compound

HRID 2255272Notes

Reaction equation

HRID 2255272 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](O)=O)=[CH:4][CH:3]=1.[CH3:12]N.N.[CH2:15]1[CH:24]2[CH:19](CCC3C=CC=C[C:23]=32)[NH:18][C:17](=[O:29])[CH2:16]1>C(O)CO.CC(O)C>[CH3:12][N:18]1[C:19]2[C@@:8]([CH3:9])([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=3[CH2:23][CH:24]=2)[CH2:15][CH2:16][C:17]1=[O:29].[CH3:12][N:18]1[C@H:19]2[C@@:8]([CH3:9])([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=3[CH2:23][CH2:24]2)[CH2:15][CH2:16][C:17]1=[O:29]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6329MethylamineHCID 15880(4-Chlorophenyl)acetic acidHCID 19707357HCID 19707357, compound

Product 2

HCID 10106832HCID 10106832, compoundHCID 18654192HCID 18654192, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 3776IsopropanolSolvent

Procedure

By following the procedures described in Example 40, Steps A, B, C, D, E and F using p-chlorophenylacetic acid as the starting material and in Step F using methylamine rather than ammonia and 2-propanol rather than ethylene glycol, the compound (R)(+) 4-methyl-8-chloro-10b-methyl-1,2,3,4,6,10b-hexahydro-benzo[f]quinolin-3-one was prepared. This hexahydrobenzo[f]quinolin-3-one was reduced according to the procedure described in Example 40, Step G. The crude product was purified by chromatography on SiO2 (ethyl acetate as eluent) to afford 5.6 g of the title compound as a pale oil which solidified on standing. Melting point 60°-61° C.

Workup

  1. customThe crude product was purified by chromatography on SiO2 (ethyl acetate as eluent)

Sources & evidence

ORD record
ord-ee1c5ba2cd9a4db79c27bfa58f80510d
Source dataset
uspto-grants-1993_08
Patent number
US05239075

Reaction notes

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