Ethanol → HCID 13787376, compound

HRID 2413936Notes

Reaction equation

HRID 2413936 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6](Cl)=[CH:7][CH:8]=2)[N:3]=1.C(O)C.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6115AnilineHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13787376HCID 13787376, compoundYield 60.8%

Conditions

Temperature
120 °C

Procedure

A suspension of 2-amino-7-chloro-1,8-naphthyridine (9 g) in aniline (19.6 g) is heated for 19 hours at 120° C. The suspension obtained is filtered, washed with diethyl ether (3×15 cc) and air-dried. The crude solid obtained (14 g; m.p. 190° C.) is then dissolved in boiling ethanol (700 cc). After cooling for 2 hours at 4° C., the crystallized product is separated by filtration, washed with ethanol (25 cc) and air-dried. 2-Amino-7-anilino-1,8-naphthyridine (7.2 g), m.p. approximately 250° C., is obtained.

Workup

  1. customThe suspension obtained
  2. filtrationis filtered
  3. washwashed with diethyl ether (3×15 cc)
  4. customair-dried
  5. customThe crude solid obtained (14 g; m.p. 190° C.)
  6. dissolutionis then dissolved
  7. temperatureAfter cooling for 2 hours at 4° C.
  8. customthe crystallized product is separated by filtration
  9. washwashed with ethanol (25 cc)
  10. customair-dried

Sources & evidence

ORD record
ord-e62183325161482e973bedeb87b2864c
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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