Sodium Acetate → HCID 11630741, compound

HRID 2172151Notes

Reaction equation

HRID 2172151 reaction equation
[CH:1]([CH:3]([CH:13]=O)[C:4]1[N:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][CH:5]=1)=O.Cl.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][NH2:25])=[CH:20][CH:19]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH:1]=[C:3]([C:4]3[N:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][CH:5]=3)[CH:13]=[N:25]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 27352046-(1,3-Dioxopropan-2-yl)pyridine-2-carboxylic acid

Product 1

HCID 11630741HCID 11630741, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6-(diformylmethyl)-pyridin-2-carboxylic acid (315 mg, 1.63 mmol), 4-methoxyphenylhydrazine hydrochloride (285 mg, 1.63 mmol) and sodium acetate (134 mg, 1.63 mmol) in acetic acid (5 mL) is heated to 110° C. for 18 h. After being allowed to cool, the solution is filtered. The solid product is washed with ethyl acetate and diethyl ether, and dried under vacuum to afford the title product (294 mg, 0.99 mmol, 61%) as a beige powder. m.p. 122-123° C. 1H NMR (300 MHz, DMSO-d6): δ 9.11 (1H, s), 8.38 (1H, s), 7.99 (2H, d, J=4.7 Hz), 7.86 (1H, t, J=4.4 Hz), 7.80 (2H, d, J=9.1 Hz), 7.08 (2H, d, J=9.1 Hz), 3.80 (3H, s), 1H missing. MS (ES+): m/e 297 (18), 296 (100). MS (ES−): m/e 295 (14), 294 (100).

Workup

  1. temperatureto cool
  2. filtrationthe solution is filtered
  3. washThe solid product is washed with ethyl acetate and diethyl ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ead393ce1a5147838c4fe00b3a13a71c
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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