Sodium Acetate → Ethyl 5-amino-1-(4-(trifluoromethoxy)phenyl)-1H-pyrazole-4-carboxylate

HRID 1496927Notes

Reaction equation

[C:1](/[C:3](=[CH:9]\OCC)/[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].Cl.[F:14][C:15]([F:26])([F:25])[O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[CH:19][CH:18]=1.CC([O-])=O.[Na+]>CC(O)=O.O>[NH2:2][C:1]1[N:23]([C:20]2[CH:19]=[CH:18][C:17]([O:16][C:15]([F:25])([F:26])[F:14])=[CH:22][CH:21]=2)[N:24]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl (2E)-2-cyano-3-ethoxy-2-propenoate (113) (1.87 g, 11.1 mmol), 4-(trifluoromethoxy)phenylhydrazine hydrochloride (114) (2.286 g, 10.00 mmol) and NaOAc (0.90 g, 11.0 mmol) in AcOH (7.5 mL) and water (2.5 mL) was heated to 100° C. under N2 for 15 h. The mixture was poured onto ice, and the resulting precipitate was filtered and recrystallised (MeOH/water) to give ethyl 5-amino-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole-4-carboxylate (115) (2.965 g, 94%) as white flakes: mp 102-103° C.; 1H NMR [(CD3)2SO] δ 7.73 (s, 1H), 7.68 (d, J=9.1 Hz, 2H), 7.53 (d, J=9.1 Hz, 2H), 6.41 (br s, 2H), 4.22 (q, J=7.1 Hz, 2H), 1.27 (t, J=7.1 Hz, 3H). APCI MS m/z 316 [M+H]+.

Workup

additionThe mixture was poured onto ice
filtrationthe resulting precipitate was filtered
customrecrystallised (MeOH/water)

Sources & evidence

ORD record: ord-0345ace1020144c48feaca8026f9560f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09198913B2

Reaction notes

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