2-Fluoroisonicotinic acid → HCID 52951819, compound

HRID 2273630Notes

Reaction equation

HRID 2273630 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].IC1C=C2C(=CC=1)N=C(C(O[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=O)C=N2>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([O:7][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:6]

Participants

3

Reactant 2

HCID 3453602-Fluoroisonicotinic acidHCID 58151992HCID 58151992, compound

Product 1

HCID 52951819HCID 52951819, compoundYield 61%

Procedure

This compound was prepared starting from compound 27 (1.00 g, 7.09 mmol), according to the procedure developed for compound 24. Reaction time at reflux: 3.5 h, reaction time at 50° C.: 12 h to give compound 35 (1.14 g, 4.35 mmol) as a white solid. Yield 61%; mp 148-150° C.; IR (KBr) ν 1220, 1283, 1406, 1525, 1742 cm−1; 1H NMR (200 MHz, CDCl3) δ 7.44 (d, 2H, J=9.3 Hz), 7.66 (m, 1H), 7.91 (td, 1H, 5JH-F=1.5 Hz, J=1.5, 5.1 Hz), 8.36 (d, 2H, J=9.3 Hz), 8.50 (d, 1H, J=5.1 Hz); MS m/z 262 (M+, 4), 124 (100), 96 (59), 76 (18), 69 (16), 63 (12), 51 (10).

Workup

  1. customThis compound was prepared
  2. customReaction time
  3. temperatureat reflux
  4. custom3.5 h, reaction time at 50° C.

Sources & evidence

ORD record
ord-514e443be3434c10983fd48537751d69
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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