6-Chloronicotinic acid → HCID 178515893, compound

HRID 2218378Notes

Reaction equation

HRID 2218378 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.Cl[C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=O)=[CH:13][N:12]=1.C(=O)([O-])[OH:21].[Na+]>>[Br:9][C:5]1[CH:6]=[C:7]2[N:8]=[C:15]([C:14]3[CH:18]=[CH:19][C:11]([OH:21])=[N:12][CH:13]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 792226-Chloronicotinic acidHCID 516892Sodium BicarbonateHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 178515893HCID 178515893, compoundYield 53%

Conditions

Temperature
140 °C

Procedure

Polyphosphoric acid (3 g) was heated to 140° C. and 2,3-diamino-5-bromopyridine (417 mg, 2.22-mmol) and 6-chloronicotinic acid (525 mg, 3.33 mmol) were added. The reaction mixture was stirred overnight at 140° C. After cooling, ice was added and the pH adjusted to 7 with a saturated solution of sodium hydrogen carbonate. A precipitate was formed which was filtered off and washed with ethyl acetate to afford the title compound (341 mg, 53%).

Workup

  1. temperatureAfter cooling
  2. additionice was added
  3. customA precipitate was formed which
  4. filtrationwas filtered off
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-e3b5cbcbc80f4073a8fcffe202fdee6a
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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