Nitrogen → Thieno[2,3-b]pyridine-5,6-dicarboxylic acid anhydride

HRID 256120Notes

Reaction equation

HRID 256120 reaction equation
C(OC(=O)C)(=O)C.[S:8]1[C:12]2=[N:13][C:14]([C:20]([OH:22])=[O:21])=[C:15]([C:17]([OH:19])=O)[CH:16]=[C:11]2[CH:10]=[CH:9]1.N#N.N1C=CC=CC=1>C(COC)OC>[S:8]1[C:12]2=[N:13][C:14]3[C:20](=[O:21])[O:22][C:17](=[O:19])[C:15]=3[CH:16]=[C:11]2[CH:10]=[CH:9]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 13729663Thieno[2,3-b]pyridine-5,6-dicarboxylic acid

Product 1

HCID 13849605Thieno[2,3-b]pyridine-5,6-dicarboxylic acid anhydrideYield 75.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Acetic anhydride (37.4 g, 0.366 mol) is added to a stirred suspension of thieno[2,3-b]pyridine-5,6-dicarboxylic acid (21.52 g, 0.096 mol) in dimethoxyethane (175 mL) in an inert N2 atmosphere. Upon addition of pyridine (16.78 g, 0.21 mol) at room temperature an exotherm to 45° C. is observed and a homogeneous solution results. The reaction mixture is then stirred at room temperature and the resulting solid filtered off, washed with ether and air dried to give 14.8 g (75%) of thieno[2,3-b]pyridine-5,6-dicarboxylic acid anhydride.

Workup

  1. customa homogeneous solution results
  2. filtrationthe resulting solid filtered off
  3. washwashed with ether and air
  4. customdried

Sources & evidence

ORD record
ord-0015f4ca5e3d4f2291b9ceacc35282a2
Source dataset
uspto-grants-1987_10
Patent number
US04701208

Reaction notes

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