Hydrochloric Acid → Methyl 2-(3-amino-4-chlorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 2045553Notes

Reaction equation

HRID 2045553 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[N+:24]([O-])=O.Cl>C(O)C.O.[Fe]>[NH2:24][C:3]1[CH:4]=[C:5]([CH:8]2[C:17]([CH3:18])([CH3:19])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=3)[NH:9]2)[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67443541Methyl 2-(4-chloro-3-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 67441358Methyl 2-(3-amino-4-chlorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylateYield 15.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of methyl 2-(4-chloro-3-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (2.82 g, 7.53 mmol) in ethanol/water (30 mL/7.5 mL) was added 0.5 mL of concentrated hydrochloric acid solution and iron powder (4.21 g, 75.3 mmol). The resultant mixture was stirred and heated to reflux for 4 h. LC-MS showed the reaction was complete. The reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated and the residue was purified by column chromatography on silica gel to afford 400 mg of methyl 2-(3-amino-4-chlorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a solid. Yield: 15%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2fe5ed1aafbb413494dc8793de451842
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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