HCID 67441792, compound → HCID 67441304, compound

HRID 1800877Notes

Reaction equation

HRID 1800877 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:26])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=1)[C:11]([CH3:25])([CH3:24])[CH2:10]2)=[O:4]>C(O)C.Cl.[Fe]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:26])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1)[C:11]([CH3:24])([CH3:25])[CH2:10]2)=[O:4]

Participants

5

Reactant 1

HCID 67441792HCID 67441792, compound

Product 1

HCID 67441304HCID 67441304, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 6-chloro-3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (1 g, 2.7 mmol) in ethanol 95% (100 mL) and 10% hydrochloric acid (5 mL) was added iron (0.23 g, 4 mmol). The reaction mixture was stirred at 95° C. for 4 h. Then the insoluble solid was filtered off and the filtrate was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with 30% sodium hydroxide in water (2×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-(3-amino-phenyl)-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (0.8 g, 86%) as a white solid: LC/MS m/e calcd for C19H21ClN2O2 (M+H)+: 345.84, observed: 345.1.

Workup

  1. filtrationThen the insoluble solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. extractionthe residue was extracted with ethyl acetate (2×200 mL)
  4. washwashed with 30% sodium hydroxide in water (2×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fee63c53ec5a4aa492065d6ab7300e36
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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