5-Amino-1-naphthol → 4-Fluoro-N-(5-hydroxynaphthalen-1-yl)-3-nitrobenzamide

HRID 326169

Reaction equation

HRID 326169 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[F:13])[C:7](Cl)=[O:8])([O-:3])=[O:2].[NH2:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[C:20]2[OH:25]>C(#N)C.CN(C)C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[F:13])[C:7]([NH:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[C:20]2[OH:25])=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 657465-Amino-1-naphtholHCID 27833474-Fluoro-3-nitrobenzoyl chloride

Product 1

HCID 204625984-Fluoro-N-(5-hydroxynaphthalen-1-yl)-3-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 949N,N-DimethylanilineSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

22.4 g of 3-nitro-4-fluorobenzoyl chloride (0.12 mols) were added dropwise at 0° C. to a suspension of 19.1 g of 5-amino-1-naphthol (0.12 mols) in 120 ml of acetonitrile and 14.2 g of N,N-dimethylaniline. The mixture was further stirred until it reached room temperature, and then heated for 30 minutes at 50° C. The yellow deposit was suction filtered and washed with acetonitrile. The deposit was dissolved in tetrahydrofurane and stirred with charcoal, filtered and the product was precipitated from the filtrate with petrol 50/75. Yield: 25.8 g=66% of the theoretical yield; mp. 235°-238° C.

Workup

  1. customreached room temperature
  2. filtrationThe yellow deposit was suction filtered
  3. washwashed with acetonitrile
  4. dissolutionThe deposit was dissolved in tetrahydrofurane
  5. stirringstirred with charcoal
  6. filtrationfiltered
  7. customthe product was precipitated from the filtrate with petrol 50/75

Sources & evidence

ORD record
ord-6d33a443335a4931be334c29a34512c5
Source dataset
uspto-grants-1984_04
Patent number
US04444867

Linked notes

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