Hydrochloric Acid → Methyl 2-benzamido-3-[(pyridin-2-yl)amino]prop-2-enoate

HRID 2109506Notes

Reaction equation

[C:1]([NH:9][C:10](=[CH:15][N:16]([CH3:18])C)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=CN=1.Cl>C(O)(C)C>[C:1]([NH:9][C:10](=[CH:15][NH:16][C:18]1[CH:23]=[CH:24][CH:25]=[CH:20][N:19]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 10 °C

Procedure

10g (39.5 mmol) of methyl 2-benzoylamino-3-dimethylaminoacrylate and 11.3 g (118 mmol) of 2-aminopyridine were dissolved in 200 ml of isopropanol at 40° C. The solution was admixed with 3.96 ml (48 mmol) of concentrated hydrochloric acid within 5 minutes (min) and stirred for a further 30 min. The suspension was cooled to 10° C. and the crystallized product was filtered off. Yield: 7.3 g (60% of theory) 1H NMR: 3.62 (s, 3H); 6.92-6.97 (m, 1H); 7.02 (d, 1H); 7.45-7.70 (m, 4H); 8.02 (d, 2H); 8.22-8.24 (m, 1H); 8.60 (d, 1H); 9.22 (s, 1 H); 9.45 (d, 1 H)

Workup

filtrationthe crystallized product was filtered off

Sources & evidence

ORD record: ord-6689eee806ab461d957c65ed6687c708
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514578B2

Reaction notes

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