Succinic anhydride → HCID 89449968, compound

HRID 525992Notes

Reaction equation

HRID 525992 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH2:12][CH2:11]1>O1CCCC1>[C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[N:7][CH:6]=1)#[N:9]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 8182602-Amino-5-cyanopyridine

Product 1

HCID 89449968HCID 89449968, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

The 6-amino-3-pyridinecarbonitrile (commercially available, 1.0 g, 8.40 mmol) was dissolved in tetrahydrofuran (20 mL) then succinic anhydride (1.04 g, 10.5 mmol) was added, the mixture was stirred at 100° C. for 12 h. The reaction was stopped and the solution was washed with a saturated solution of sodium carbonate. The organic layer was concentrated under vacuum. The residue was purified by flash chromatography eluting with methanol-ethyl acetate (5/95) to give 4-[(5-cyano-2-pyridyl)amino]-4-oxo-butanoic acid A2 (0.325 g, 18%). M.p.=220-221° C., 1H NMR (400 MHz, DMSO-d6) δ 12.18 (bs, 1H), 11.04 (s, 1H), 8.78 (s, 1H), 8.21 (m, 2H), 2.69 (t, 2H), 2.52 (m, 2H) ppm. LC-MS (Method B): RT 1.00, 218 (M−H+) The following compounds from table A were prepared by the same method:

Workup

  1. washthe solution was washed with a saturated solution of sodium carbonate
  2. concentrationThe organic layer was concentrated under vacuum
  3. customThe residue was purified by flash chromatography
  4. washeluting with methanol-ethyl acetate (5/95)

Sources & evidence

ORD record
ord-3bfe565d9f32485baac04caa35276307
Source dataset
uspto-grants-2016_05
Patent number
US09345244B2

Reaction notes

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