Ammonia → HCID 178507291, compound

HRID 256513Notes

Reaction equation

HRID 256513 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4][C:5]([O:7]CC)=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[N:13]=1.P(=O)(O)(O)O.N>>[NH2:18][C:14]1[CH:15]=[CH:16][C:17]2[C:12](=[N:11][C:5]([OH:7])=[CH:4][C:3]=2[CH2:2][Cl:1])[N:13]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 1004Phosphoric AcidHCID 88612,6-DiaminopyridineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 178507291HCID 178507291, compoundYield 54.4%

Conditions

Temperature
90 °C

Procedure

32.9 g (0.2 mol) of ethyl 4-chloroacetoacetate is dripped into a suspension of 21.8 g (0.2 mol) of 2,6-diaminopyridine in 100 ml of 85% strength phosphoric acid. The reaction mixture is stirred for 3 hours at 90° C., cooled and poured into ice water, followed by neutralization with concentrated aqueous ammonia solution. The precipitate is suction filtered, stirred into water again and finally boiled with acetonitrile. 22.8 g (54%) of the title compound is obtained; m.p.: >280° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. stirringstirred into water again

Sources & evidence

ORD record
ord-8272b810451d40608f12ec452d698c7b
Source dataset
uspto-grants-1993_11
Patent number
US05258356

Reaction notes

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