Phosphoric Acid → HCID 23335406, compound

HRID 2163330Notes

Reaction equation

HRID 2163330 reaction equation
P(=O)(O)(O)O.[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[N:8]=1.[CH3:14][CH2:15][C:16](=O)[CH2:17][C:18](=O)[CH2:19][CH3:20]>>[NH2:6][C:7]1[CH:12]=[CH:11][C:10]2[C:9](=[N:13][C:16]([CH2:15][CH3:14])=[CH:17][C:18]=2[CH2:19][CH3:20])[N:8]=1

Participants

4

Reactant 3

HCID 1004Phosphoric AcidHCID 88612,6-DiaminopyridineHCID 819233,5-Heptanedione

Product 1

HCID 23335406HCID 23335406, compound

Procedure

To 50 ml. of 85% phosphoric acid is added with stirring 2,6-diaminopyrdine (6.55 g., 0.06 mole) followed by 3,5-heptanedione (7.7 g., 0.06 mole). The mixture is heated on the steam bath under nitrogen atmosphere for 16 hours. The reaction mixture is poured into crushed ice and neutralized with concentrated ammonium hydroxide and extracted with methylene chloride (3 × 250 ml.). The combined extracts are dried, filtered and concentrated in vacuo. Crystallization of the residue from ethyl acetate affords 2-amino-5,7-diethyl-1,8-naphthyridine melting at 187°-189° C.

Workup

  1. temperatureThe mixture is heated on the steam bath under nitrogen atmosphere for 16 hours
  2. additionThe reaction mixture is poured
  3. custominto crushed ice
  4. extractionneutralized with concentrated ammonium hydroxide and extracted with methylene chloride (3 × 250 ml.)
  5. customThe combined extracts are dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customCrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-5454a8d4ed5a4a93a9b644d5d067e767
Source dataset
uspto-grants-1979_01
Patent number
US04133885

Reaction notes

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