Water → HCID 66817303, compound

HRID 1697104Notes

Reaction equation

HRID 1697104 reaction equation
Br[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[N:14]=1.C([O-])([O-])=O.[K+].[K+].O>C(OC(O)C)C>[NH2:12][C:13]1[N:14]=[C:15]([NH:19][C:2]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 88612,6-DiaminopyridineHCID 11430Potassium CarbonateHCID 331262-Bromo-4-chlorobenzoic acid

Product 1

HCID 66817303HCID 66817303, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 101298981-EthoxyethanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-bromo-4-chlorobenzoic acid (5 g), 2,6-diaminopyridine (6.95 g), K2CO3 (3.18 g), Cu powder (0.13 g) and Cu(I) oxide (0.15 g) in ethoxyethanol (10 mL) was heated at 130° C. for 2 h, until the reaction was complete (as confirmed by tlc). The mixture was cooled to RT, and water (70 mL) and activated carbon was added, and the mixture stirred for 3 h. The product was then filtered, and HCl (4 M) was added until pH 7 was reached. The resulting brown precipitate was filtered and dried in an oven (50° C., pressure=30 mbar) overnight to provide 2-(6-amino-pyridin-2-ylamino)-4-chlorobenzoic acid (2.4 g).

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe product was then filtered
  3. additionHCl (4 M) was added until pH 7
  4. filtrationThe resulting brown precipitate was filtered
  5. customdried in an oven (50° C., pressure=30 mbar) overnight

Sources & evidence

ORD record
ord-d5da9ba57c4e4ce0b1f5e8356ecd1934
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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