Water → 1-Naphthanilide

HRID 905515Notes

Reaction equation

HRID 905515 reaction equation
[C:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.[OH-].[NH4+]>C(#N)C.C(OCC)C>[C:15]1([NH:14][C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[O:12])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 14923Ammonium HydroxideHCID 701461-Naphthalenecarbonyl chloride

Product 1

HCID 3471821-NaphthanilideYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
82 °C

Procedure

4.77 g of 1-naphthoyl chloride (TCI America) was dissolved in 100 ml of anhydrous acetonitrile. To the solution so formed, 2.28 ml of aniline (Sigma-Aldrich) was added in a dropwise fashion over a period of c.a. 20 min. The reaction was then refluxed for 2 h at 82° C. 100 ml of distilled water and 5 ml of concentrated ammonium hydroxide were added along with 100 ml of diethyl ether in a separatory funnel. The phases were separated and the aqueous phase was washed with 100 ml of dichloromethane. The organic fractions were collected and dried with magnesium sulfate, filtered and the solvent was then removed under reduced pressure to yield a white solid 5.07 g (82%; 20.5 mmol).

Workup

  1. customTo the solution so formed
  2. custom20 min
  3. customThe phases were separated
  4. washthe aqueous phase was washed with 100 ml of dichloromethane
  5. customThe organic fractions were collected
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-cb5847bc2b8849bfbcea377930f23d20
Source dataset
uspto-grants-2011_09
Patent number
US08012458B2

Reaction notes

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