2-Aminonicotinic acid → HCID 67388390, compound

HRID 908424Notes

Reaction equation

HRID 908424 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1O>>[F:18][C:14]1[C:13]2[O:6][C:4]([C:3]3[C:2]([NH2:1])=[N:10][CH:9]=[CH:8][CH:7]=3)=[N:11][C:12]=2[CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 729302-Aminonicotinic acidHCID 6435622-Amino-6-fluorophenol

Product 1

HCID 67388390HCID 67388390, compoundYield 48.1%

Conditions

Temperature
200 °C

Procedure

A mixture of 2-aminonicotinic acid (9.4 g), 2-amino-6-fluoro-phenol (8.65 g) and polyphosphoric acid (90 g) was stirred at 200° C. for 16 hours. The reaction mixture was allowed to cool to room temperature, quenched with water and basified with sodium hydroxide solution 6N until pH 12 to give a solid which was collected by filtration and dried under vacuum; The resultant product was diluted in dichloromethane/methanol and filtered through a plug of silica gel and washed with ethyl acetate. The filtrate was concentrated to dryness to give 3-(7-fluoro-1,3-benzoxazol-2-yl)pyridin-2-amine (7.5 g) as a solid. NMR Spectrum: (DMSOd6) 6.76 (dd, 1H), 7.33-7.46 (m, 2H), 7.66 (bs, 2H), 7.68 (dd, 1H), 8.26 (dd, 1H), 8.30 (dd, 1H); Mass spectrum: M+H+ 230.

Workup

  1. temperatureto cool to room temperature
  2. customquenched with water
  3. customto give a solid which
  4. filtrationwas collected by filtration
  5. customdried under vacuum
  6. additionThe resultant product was diluted in dichloromethane/methanol
  7. filtrationfiltered through a plug of silica gel
  8. washwashed with ethyl acetate
  9. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-0d62188302f14da6aa93175bef412d2d
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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