2-Aminonicotinic acid → HCID 45103347, compound

HRID 908427Notes

Reaction equation

HRID 908427 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[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1O>>[F:18][C:17]1[C:12]2[N:11]=[C:4]([C:3]3[C:2]([NH2:1])=[N:10][CH:9]=[CH:8][CH:7]=3)[O:6][C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 729302-Aminonicotinic acidHCID 27827782-amino-3-fluorophenol

Product 1

HCID 45103347HCID 45103347, compoundYield 62.1%

Conditions

Temperature
200 °C

Procedure

PPA (10 ml) at 50° C. was added to a stirred mixture of 2-aminonicotinic acid (2 g) and 2-amino-3-fluoro-phenol (1.841 g). The resulting suspension was stirred at 200° C. for 16 hours. The mixture was cooled and quenched with ice and water (100 ml) and the pH was adjusted to 12 with an aqueous solution of sodium hydroxide (6N then 2N). The resultant solid was filtered and washed with water. The solid was dried under reduce pressure with phosphorus pentoxide. The solid was adsorbed on silica gel with methylene chloride (100 ml) and methanol (10 ml) and purified by flash chromatography on silica gel eluting with 20 to 30% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford 3-(4-fluoro-1,3-benzoxazol-2-yl)pyridin-2-amine (2.060 g) as a solid. NMR Spectrum: (CDCl3): 6.78 (dd, 1H), 6.97 (bs, 2H), 7.09 (dd, 1H), 7.31 (ddd, 1H), 7.38 (d, 1H), 8.30 (d, 1H), 8.33 (bs, 1H); Mass spectrum: M+H+ 230

Workup

  1. temperatureThe mixture was cooled
  2. customquenched with ice and water (100 ml)
  3. filtrationThe resultant solid was filtered
  4. washwashed with water
  5. customThe solid was dried
  6. custompurified by flash chromatography on silica gel eluting with 20 to 30% ethyl acetate in dichloromethane
  7. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-071b48e0576046c6b842cae4f97c4c09
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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