Hydrochloric Acid → 2-Methoxybenzoic acid

HRID 2051609Notes

Reaction equation

HRID 2051609 reaction equation
COC(Cl)=O.ClC1C=NC(OC2CCCCC2)=C(C=1)C(O)=O.NCC[C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[C:28]([O:35][CH3:36])[CH:27]=1.Cl>O1CCCC1.C(N(CC)CC)C>[CH3:36][O:35][C:28]1[CH:27]=[CH:26][CH:34]=[CH:33][C:29]=1[C:30]([OH:32])=[O:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 20266354HCID 20266354, compoundHCID 20379240HCID 20379240, compound

Product 1

HCID 113702-Methoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

6 g of triethylamine and 1.9 g of chloroformic acid methyl ester are added, while stirring and cooling with ice, to 5 g of 5-chloro-2-cyclohexyloxy-nicotinic acid in 150 ml of tetrahydrofuran. Stirring is continued for 30 minutes at 0° C. and, while stirring, 4.6 g of 4-(2-aminoethyl)-2-methoxybenzoic acid are added in the form of its hydrochloride. The mixture is further stirred for 4 hours at room temperature, the solvent removed under reduced pressure, the residue reprecipitated from ammonia and recrystallized from ethanol or ethyl acetate. The 4-(2-<5-chloro-2-cyclohexyloxy-nicotinamido>-ethyl)-2-methoxy-benzoic acid obtained melts at 170°-172° C.

Workup

  1. stirringStirring
  2. stirringwhile stirring
  3. stirringThe mixture is further stirred for 4 hours at room temperature
  4. customthe solvent removed under reduced pressure
  5. customthe residue reprecipitated from ammonia
  6. customrecrystallized from ethanol or ethyl acetate

Sources & evidence

ORD record
ord-b0975c33df7f4524ade1ca1c3932d166
Source dataset
uspto-grants-1980_01
Patent number
US04181658

Reaction notes

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