HCID 67290739, compound → HCID 67290769, compound

HRID 1036873Notes

Reaction equation

HRID 1036873 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O)[CH2:6][C:5]2([CH3:22])[CH3:21]>C(O)C.Cl.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])[CH2:6][C:5]2([CH3:22])[CH3:21]

Participants

5

Reactant 1

HCID 67290739HCID 67290739, compound

Product 1

HCID 67290769HCID 67290769, compoundYield 35.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 6-chloro-4,4-dimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (7.7 g, 24.3 mmol) in ethanol and 10% hydrochloric acid was added iron powder (7.0 g, 125.4 mmol). The resulting mixture was stirred at 90° C. for 3 h. Then the insoluble solid was filtered off and the filtrate was concentrated in vacuum. The residue was extracted with ethyl acetate, washed with saturated sodium carbonate, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography to give 2-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)aniline (2.5 g, yield 35.7%) LC/MS m/e obsd. (ESI+) [(M+H)+] 287.2.

Workup

  1. filtrationThen the insoluble solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuum
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with saturated sodium carbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5333704b6cf14cf09eea163feec67d67
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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