Chloroacetyl chloride → 1-(Chloroacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 514276Notes

Reaction equation

HRID 514276 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:14][CH2:15][C:16](Cl)=[O:17].C(OCC)(=O)C.CCCCCCC>C(OCC)(=O)C>[Cl:14][CH2:15][C:16]([N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH2:8][CH2:9][CH2:10]1)=[O:17]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 2525137-Nitro-1,2,3,4-tetrahydroquinolineHCID 21899848Ethylacetate heptane

Product 1

HCID 125783601-(Chloroacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

1.78 g of 7-nitro-1,2,3,4-tetrahydroquinoline (0.01 mol) are dissolved in 15 ml of ethyl acetate. This solution is run into a mixture of 15 ml of ethyl acetate and 0.80 ml of chloroacetyl chloride. A white precipitate forms immediately, and stirring is continued at 30° C. for 2 h (the reaction is monitored by thin layer chromatography (90/10 ethyl acetate/heptane)). After 2 h, since the reaction is incomplete, 0.2 equivalent of chloroacetyl chloride is added and the temperature is raised to 60° C.; the solid formed undergoes dissolution. When the reaction has finished, the mixture is cooled and the solvent is evaporated off. 2.46 g of a beige product which corresponds to the expected compound are recovered.

Workup

  1. waitAfter 2 h
  2. customthe solid formed
  3. dissolutionundergoes dissolution
  4. temperaturethe mixture is cooled
  5. customthe solvent is evaporated off
  6. customare recovered

Sources & evidence

ORD record
ord-593036ff0b084698885f21b3a9eaebfa
Source dataset
uspto-grants-2015_08
Patent number
US09107848B2

Reaction notes

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