Formaldehyde → HCID 22346322, compound

HRID 897342Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][O:8][C:9]2[C:10]([C:21]([O:23][CH3:24])=[O:22])=[N:11][C:12]([CH:19]=[CH2:20])=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)=[CH:5][CH:4]=1.[CH2:27]=O.[C:29]([NH:32][NH:33][CH3:34])(=[O:31])[CH3:30]>C1(C)C=CC=CC=1>[C:29]([N:32]1[CH:19]([C:12]2[N:11]=[C:10]([C:21]([O:23][CH3:24])=[O:22])[C:9]([O:8][CH2:7][C:6]3[CH:25]=[CH:26][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[C:18]3[C:13]=2[CH:14]=[CH:15][CH:16]=[N:17]3)[CH2:20][CH2:34][N:33]1[CH3:27])(=[O:31])[CH3:30]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of methyl 8-[(4-methoxybenzyl)oxy]-5-vinyl-[1,6]-naphthyridine-7-carboxylate (0.26 g, 0.73 mmol), paraformaldehyde (96 mg), and 1-acetyl-2-methylhydrazine (0.22 g, 2.45 mmol; J. Org. Chem. 1972, 37, 3608) in toluene (15 mL) was heated in an oil bath at 120° C. for 1.5 hour. The resulting mixture was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting first with a gradient of 0-5% methanol in ethyl acetate. Collection and concentration of appropriate fractions provided the title acetylpyrazolidine.

Workup

concentrationThe resulting mixture was concentrated under vacuum
customCollection and concentration of appropriate fractions

Sources & evidence

ORD record: ord-cea68d1b2e0d44f094406927c8188d52
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921759B2

Reaction notes

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