Hydrochloric Acid → HCID 67342117, compound

HRID 1846644Notes

Reaction equation

HRID 1846644 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH2:14]([O:16][C:17](=[O:25])[CH2:18]N1CCNCC1)[CH3:15].O.Cl>CN(C)C=O>[CH2:14]([O:16][C:17]([CH2:18][CH:9]1[CH2:5][CH2:4][N:3]([C:2]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=2)[CH2:2][CH2:10]1)=[O:25])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 207112Ethyl piperazine-1-acetateHCID 3464596-CHLORO-5-NITRONICOTINIC ACID

Product 1

HCID 67342117HCID 67342117, compoundYield 162.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2.00 g (9.87 mmol) of 6-chloro-5-nitro-nicotinic acid and 2.03 g (11.8 mmol) of piperazin-1-yl-acetic acid ethyl ester in N,N-dimethylformamide (10 mL) are heated to 130° C. in a microwave reactor for 1 hour. The resulting dark mixture is poured into water which forms a precipitate. The pH of the mixture is adjusted to approximately pH 2 by adding concentrated hydrochloric acid. The precipitated solid is collected by filtration, washed with water, and dried under reduced pressure to give 2.70 g (81.1%) of 4-ethoxycarbonylmethyl-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid as a yellow solid.

Workup

  1. filtrationThe precipitated solid is collected by filtration
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-f12f5119bee6499397c638662be3804e
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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