Ammonia → HCID 19707341, compound

HRID 726691Notes

Reaction equation

HRID 726691 reaction equation
[C:1]1([CH2:7][C:8](O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([NH2:13])[CH3:12].N.[CH2:15]1[CH:24]2[CH:19]([CH2:20][CH2:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=32)[NH:18][C:17](=[O:29])[CH2:16]1>C(O)CO>[CH2:11]([N:18]1[C:19]2[C:7]([CH3:8])([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=3[CH2:23][CH:24]=2)[CH2:15][CH2:16][C:17]1=[O:29])[CH3:12].[CH2:11]([N:13]1[C@@H:19]2[C@:24]([CH3:1])([C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[CH2:21][CH2:20]2)[CH2:15][CH2:16][C:17]1=[O:29])[CH3:12]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 999Phenylacetic AcidHCID 6341EthylamineHCID 19707357HCID 19707357, compound

Product 2

HCID 19707341HCID 19707341, compoundHCID 54248187HCID 54248187, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

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 using ethylamine rather than ammonia, and digylme rather ethylene glycol in Step F, the compound 4-ethyl-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 70° C. over 7 hours to afford a crude reaction mixture. The reaction mixture was filtered and the solvents evaporated under vacuum to afford a glassy solid residue. The crude product was purified by chromatography on SiO2 (gradient elution from 100% hexanes to 100% CHCl3) to afford 92 mg of the title compound as a colorless oil.

Workup

  1. customto afford a crude
  2. customreaction mixture
  3. filtrationThe reaction mixture was filtered
  4. customthe solvents evaporated under vacuum
  5. customto afford a glassy solid residue
  6. customThe crude product was purified by chromatography on SiO2 (gradient elution from 100% hexanes to 100% CHCl3)

Sources & evidence

ORD record
ord-15c9f1d7d0f942bdb8ee75a4cab98709
Source dataset
uspto-grants-1998_01
Patent number
US05710163

Reaction notes

Loading…