Aniline → HCID 15766434, compound
Reaction equation
[OH:1][C:2]1[C:11]([C:12]([O:14]C2C=CC=CC=2)=O)=[CH:10][C:9]2[C:4](=[C:5]([OH:21])[CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[OH:1][C:2]1[C:11]([C:12]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:14])=[CH:10][C:9]2[C:4](=[C:5]([OH:21])[CH:6]=[CH:7][CH:8]=2)[CH:3]=1Participants
Conditions
- Temperature
- 25 °C
Procedure
The aromatic ester is reacted with an aniline in a solvent and heating to form the anilide product. The reaction temperature can be varied to from about 140° C. to about 280° C. or above. Specifically, phenyl 2,8-dihydroxy-3-naphthoate can be reacted with aniline in methyl N-pyrrolidinone at about 250° C. The ratio of the phenyl ester to the aniline can vary, for example, from about 1:1 equivalent and up to about 20 equivalents. After the reaction is completed, the product mixture is cooled to room temperature, about 25° C., and discharged into an acidic aqueous solution, such as a 5 percent HCl ice cold solution. The precipitated anilide product, 2,8-dihydroxy-3-naphthanilide, is isolated by filtration and washed with water. Purification can be accomplished by first dissolving the crude product in a hot solvent, such as DMF, and then precipitating the product by adding water or methanol, or a mixture of methanol and water. The purified product is then characterized by m.p., IR, mass spectrometry, NMR spectroscopy and elemental analysis.
Workup
- customcan be varied to from about 140° C. to about 280° C. or above
Sources & evidence
- ORD record
- ord-5e36ca00283c4f45a8deeafffdc66b5f
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05302753
Reaction notes
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