6-Aminonicotinic acid → HCID 12953042, compound

HRID 1155925Notes

Reaction equation

HRID 1155925 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.O=[C:12]1[CH2:16][S:15][CH2:14][CH:13]1[C:17](OC)=[O:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[O:18]=[C:17]1[N:3]2[CH:4]=[C:5]([C:6]([OH:8])=[O:7])[CH:9]=[CH:10][C:2]2=[N:1][C:12]2[CH2:16][S:15][CH2:14][C:13]1=2

Participants

4

Reactant 3

HCID 184966-Aminonicotinic acidHCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl esterHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 12953042HCID 12953042, compoundYield 63.2%

Conditions

Temperature
170 °C

Procedure

6-Aminonicotinic acid (10 g., 0.072 mol) [Berichte, 26, 2187,(1893)], methyl 4-oxotetrahydro-thiophene-3-carboxylate (28 g., 0.175 mol) [Monats, Chem., 104, 1520(1973)]and p-toluenesulfonic acid monohydrate (1.0 g) are thoroughly mixed and heated at 170° C. under nitrogen for 75 minutes. The distillate is collected in a Dean-Stark trap. The residue is cooled, tritrated with boiling chloroform and filtered to give the product as a yellow powder (11.3 g.). Recrystallization from dimethylformamide gives an analytical sample mp 314°-315° C. (dec).

Workup

  1. distillationThe distillate is collected in a Dean-Stark trap
  2. temperatureThe residue is cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-694944df3ffb482a89e78e43a6714e06
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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