Hydrochloric Acid → HCID 22025904, compound

HRID 917616Notes

Reaction equation

HRID 917616 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][NH2:6].[C:12](=[O:15])([O-])[O-:13].[K+].[K+].[CH3:18][N:19]1[CH2:23][CH2:22][CH2:21][C:20]1=O.[ClH:25]>[Cu](Br)Br.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][NH:6][C:18]1[N:19]=[C:20]([Cl:25])[CH:21]=[CH:22][C:23]=1[C:12]([OH:13])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 7380383-Chloro-4-methoxybenzylamine

Product 1

HCID 22025904HCID 22025904, compound

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of the compound (prepared in the above (1)) 500 mg, 3-chloro-4-methoxybenzylamine 638 mg, potassium carbonate 817 mg, copper bromide 313 mg and 1-methyl-2-pyrrolidinone 10 ml is stirred at 120° C. for 2.5 hours. After cooling to room temperature thereto are added ethyl acetate and 1 N hydrochloric acid. The organic layer is separated, washed with water (twice) and brine, and dried over sodium sulfate. After removal of sodium sulfate, the filtrate is concentrated in vacuo, and the residue is purified with column chromatography (silica gel 30 g, solvent; chloroform→chloroform:methanol=70:1) to give 2-(3-chloro-4-methoxybenzylamino)-6-chloronicotinic acid as colorless crystals, 471 mg. mp 184-185.5° C., MS(m/z): 325(M−H)−

Workup

  1. additionA mixture of the compound (
  2. temperatureAfter cooling to room temperature
  3. customThe organic layer is separated
  4. washwashed with water (twice) and brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of sodium sulfate
  7. concentrationthe filtrate is concentrated in vacuo
  8. customthe residue is purified with column chromatography (silica gel 30 g, solvent; chloroform→chloroform:methanol=70:1)

Sources & evidence

ORD record
ord-a0c1140820f4460d9ad86fd4189ba2c5
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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