Hydrochloric Acid → 2-Amino-5-(2-fluoro-5-hydroxy-4-methylanilino)-1,8-naphthyridine

HRID 393661Notes

Reaction equation

HRID 393661 reaction equation
Cl.C([NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[NH:16][C:17]2[CH:22]=[C:21]([OH:23])[C:20]([CH3:24])=[CH:19][C:18]=2[F:25])[N:7]=1)(=O)C.Cl>C(O)C>[NH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[NH:16][C:17]2[CH:22]=[C:21]([OH:23])[C:20]([CH3:24])=[CH:19][C:18]=2[F:25])[N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 226465602-Acetamido-5-(2-fluoro-5-hydroxy-4-methylanilino)-1,8-naphthyridine hydrochloride

Product 1

HCID 223464762-Amino-5-(2-fluoro-5-hydroxy-4-methylanilino)-1,8-naphthyridineYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-acetamido-5-(2-fluoro-5-hydroxy-4-methylanilino)-1,8-naphthyridine hydrochloride (170 mg, 0.46 mmol), (prepared as described in Example 53), and concentrated hydrochloric acid (0.5 ml) in ethanol (10 ml) was heated at reflux for 2 hours. The mixture was allowed to cool and the organic volatiles were removed by evaporation. The aqueous residue was basified to pH9 with aqueous sodium hydroxide solution and the resulting precipitate was collected by filtration, washed with water and dried to give 2-amino-5-(2-fluoro-5-hydroxy-4-methylanilino)-1,8-naphthyridine (100 mgs 76%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. customthe organic volatiles were removed by evaporation
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-3dfb93076314459db3a7ce4325c3b611
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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