HCID 42637705, compound → HCID 42637767, compound

HRID 2364126Notes

Reaction equation

HRID 2364126 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([C:16]([OH:18])=[O:17])[C:10]([C:13](O)=[O:14])=[N:11][CH:12]=2)=[CH:4][CH:3]=1>CC(OC(C)=O)=O>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][C:7]2[CH:8]=[C:9]3[C:16](=[O:18])[O:17][C:13](=[O:14])[C:10]3=[N:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 42637705HCID 42637705, compound

Product 1

HCID 42637767HCID 42637767, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-(4-fluorobenzyl)-2,3-pyridinedicarboxylic acid (25.3 g, 92 mmol) and Ac2O (200 mL) was stirred for 3 h at 120° C. The reaction mixture was concentrated in vacuo, dissolved in toluene (200 mL) and re-concentrated in vacuo again to give 5-(4-fluorobenzyl)-2,3-pyridinedicarboxylic anhydride. This material was dissolved in EtOH (200 mL) and the mixture was heated at reflux for 3 h and then stored at rt overnight. The reaction mixture was concentrated in vacuo, dissolved in toluene and concentrated again to afford the product as the major isomer. This material contained ca. 30% of the corresponding 3-ethyl ester 2-carboxylic acid isomer. Major isomer: 1H NMR (d6-DMSO) δ 13.5 (1H, br), 8.67 (1H, d, J=2 Hz), 8.06 (1H, d, J=2 Hz), 7.31 (2H, dd, J˜9, 6 Hz), 7.11 (2H, t, J˜9 Hz), 4.25 (2H, q, J=7 Hz), 1.24 (3H, t, J=7 Hz); ES+ MS: 304 (M+H+, 80), 326 (M+Na+, 30).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in toluene (200 mL)
  3. concentrationre-concentrated in vacuo again

Sources & evidence

ORD record
ord-96951ed5ba8941018d74536ca0fbffd7
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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