Ammonium Chloride → HCID 67290882, compound

HRID 1036907Notes

Reaction equation

HRID 1036907 reaction equation
[CH3:1][C:2]1([CH3:26])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[NH:5][CH:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-])=O)[CH2:3]1.[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:4]1[CH2:3][C:2]([CH3:1])([CH3:26])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[NH:5]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67292481HCID 67292481, compound

Product 1

HCID 67290882HCID 67290882, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred suspension of ethyl 4,4-dimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (13.0 g, 36.7 mmol) in ethanol was added iron powder (8.2 g, 146.7 mmol) and saturated aqueous ammonium chloride sat room temperature, the reaction mixture was stirred at 90° C. for 3 h. The insoluble solid was filtered off and filtrated was concentrated in vacuum and the residue was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated in vacuum. The residue was purified by column chromatography to give ethyl 2-(2-aminophenyl)-4,4-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as yellow solid (5.4 g, yield 45.4%). LC/MS m/e obsd. (ESI+) [(M+H)+] 325.1.

Workup

  1. customsat room temperature
  2. filtrationThe insoluble solid was filtered off
  3. filtrationfiltrated
  4. concentrationwas concentrated in vacuum
  5. extractionthe residue was extracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-abae530e54b749f3b5a0c38614af91c5
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

Loading…