Acetic Anhydride → HCID 19068578, compound

HRID 1957088Notes

Reaction equation

O=[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH:4]=[CH:3]1.[CH2:17]([O:25][C:26](=[O:30])[CH2:27][C:28]#[N:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(OC(=O)C)(=O)C>>[CH2:17]([O:25][C:26]([C:27]([C:28]#[N:29])=[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH:4]=[CH:3]1)=[O:30])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 4241808HCID 4241808, compound

HCID 4384482Octyl cyanoacetate2×

Product 1

HCID 19068578HCID 19068578, compoundYield 85%

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-(4-oxo-4H-pyridin-1-yl)benzoic acid (814 mg, 3.5 mmol), octylcyanoacetate (3.44 g, 17.5 mmol) and acetic anhydride (45 ml) was heated at 130° C. for 3 hours. More octylcyanoacetate (3.44 g, 17.5 mmol) was added and the mixture heated for 3 hours more. The mixture was then filtered hot, and the filtrate was diluted with acetic acid (15 ml) and water (15 ml). Upon standing overnight in the refrigerator the product crystallized out and was isolated by suction filtration as a yellow solid (1.16 g, 85%).

Workup

temperaturethe mixture heated for 3 hours more
filtrationThe mixture was then filtered hot
additionthe filtrate was diluted with acetic acid (15 ml) and water (15 ml)
customthe product crystallized out

Sources & evidence

ORD record: ord-7b0e783c1a754eed93913826f95c2c24
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783114

Reaction notes

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