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Ammonia → HCID 19707339, compound

HRID 2255271
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Reaction equation

HRID 2255271 reaction equation
[C:1]1([CH2:7][C:8](O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][NH2:12].N.[CH2:14]1[CH:23]2[CH:18]([CH2:19][CH2:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=32)[NH:17][C:16](=[O:28])[CH2:15]1>C(O)CO.COCCOCCOC>[CH3:11][N:17]1[C:18]2[C:7]([CH3:8])([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=3[CH2:22][CH:23]=2)[CH2:14][CH2:15][C:16]1=[O:28].[CH3:11][N:12]1[C@@H:18]2[C@:23]([CH3:1])([C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[CH2:20][CH2:19]2)[CH2:14][CH2:15][C:16]1=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 222AmmoniaHCID 999Phenylacetic AcidHCID 6329MethylamineHCID 19707357HCID 19707357, compound

Product 2

HCID 19707339HCID 19707339, compoundHCID 53780108HCID 53780108, compound

Reagents, catalysts & solvents 2

HCID 174
Ethylene Glycol
Solvent
HCID 8150DiglymeSolvent

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 methylamine rather than ammonia and diglyme rather than ethylene glycol, the compound 4-methyl-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 in Example 22 except that the reaction was carried out at 60° C. over 7 hours. The reaction mixture was filtered and solvent evaporated under vacuum. The residue was purified by chromatography on SiO2 (CHCl3 as eluent) followed by recrystallization from ethyl acetate/hexanes to afford 154 mg of the title compound. Melting point 111°-113° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customsolvent evaporated under vacuum
  3. customThe residue was purified by chromatography on SiO2 (CHCl3 as eluent)
  4. customfollowed by recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ec65e3214a5b4d2180d01108b504369e
Source dataset
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05239075

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes