Methyl Nicotinate → Nicotinic Acid

HRID 2419686

Reaction equation

HRID 2419686 reaction equation
O1CCOCC1.FC(F)(F)C1C=CC([N+]([O-])=O)=CC=1N.[N+](C1C=CC(C(F)(F)F)=CC=1N)([O-])=O.C[O:36][C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[N:40][CH:39]=1>O>[C:37]([OH:44])(=[O:36])[C:38]1[CH:43]=[CH:42][CH:41]=[N:40][CH:39]=1

Participants

6

Reactant 4

HCID 7151Methyl NicotinateHCID 312751,4-DioxaneHCID 2231003-Amino-4-nitrobenzotrifluorideHCID 27377192-Amino-4-nitrobenzotrifluoride

Product 1

HCID 938Nicotinic AcidYield 46.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 20 ml of dioxan and 10 g of 2-trifluoromethyl-5-nitroaniline or 2-nitro-5-trifluoromethyl-aniline to 12 g of nicotinic acid methyl ester. Reflux for 60 hours; then pour the reaction mass into water. Filter the resulting solid and recrystallize several times from ethanol. 5 g of (I) or (III) are thus obtained with the same melting-point values as the products of Examples 1 and 3.

Workup

  1. temperatureReflux for 60 hours
  2. filtrationFilter the resulting solid
  3. customrecrystallize several times from ethanol

Sources & evidence

ORD record
ord-fa18031f90554cfdad678aafad4662a9
Source dataset
uspto-grants-1978_08
Patent number
US04107316

Linked notes

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