5-Amino-4-fluoro-2-methylphenol → 2-Acetamido-5-(2-fluoro-5-hydroxy-4-methylanilino)-1,8-naphthyridine hydrochloride

HRID 393657Notes

Reaction equation

HRID 393657 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[N:8][CH:9]=[CH:10][C:11]=2[Cl:15])[N:6]=1)(=[O:3])[CH3:2].[F:16][C:17]1[CH:23]=[C:22]([CH3:24])[C:21]([OH:25])=[CH:20][C:18]=1[NH2:19]>C(O)(C)C>[ClH:15].[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[N:8][CH:9]=[CH:10][C:11]=2[NH:19][C:18]2[CH:20]=[C:21]([OH:25])[C:22]([CH3:24])=[CH:23][C:17]=2[F:16])[N:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 101540985-Amino-4-fluoro-2-methylphenolHCID 22646664N-(5-chloro-1,8-naphthyridin-2-yl)acetamide

Product 1

HCID 226465602-Acetamido-5-(2-fluoro-5-hydroxy-4-methylanilino)-1,8-naphthyridine hydrochlorideYield 61%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-acetamido-5-chloro-1,8-naphthyridine (357 mg, 1.6 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (200 mg, 1.4 mmol), (prepared as described for the starting material in Example 1), in isopropanol (20 ml) was heated at reflux for 5 hours. The mixture was allowed to cool and the precipitate was collected by filtration, washed with acetone and dried to give 2-acetamido-5-(2-fluoro-5-hydroxy-4-methylanilino)-1,8-naphthyridine hydrochloride (280 mg, 61%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 5 hours
  4. temperatureto cool
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with acetone
  7. customdried

Sources & evidence

ORD record
ord-c6bb59ae3e7948e4beb83cabc65295ce
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

Loading…