Aniline → 2-Naphthalenecarboxamide, 3-hydroxy-7-methoxy-N-phenyl-

HRID 1198381Notes

Reaction equation

HRID 1198381 reaction equation
[OH:1][C:2]1[C:11]([C:12]([OH:14])=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:15][CH3:16])[CH:8]=2)[CH:3]=1.S(Cl)(Cl)=O.C1C=CC2C(=CC=CC=2C(O)=O)C=1.OC1C(C(Cl)=O)=CC2C(=CC=C(OC)C=2)C=1.[NH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C(N(CC)C1C=CC=CC=1)C>C(Cl)Cl.CN(C)C=O>[OH:1][C:2]1[C:11]([C:12]([NH:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:14])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:15][CH3:16])[CH:8]=2)[CH:3]=1

Participants

9

Reactant 6

HCID 6115AnilineHCID 68471-Naphthoic acidHCID 7061N,N-DiethylanilineHCID 24386Thionyl ChlorideHCID 6083303-Hydroxy-7-methoxy-2-naphthoic acidHCID 54219146HCID 54219146, compound

Product 1

HCID 1705422-Naphthalenecarboxamide, 3-hydroxy-7-methoxy-N-phenyl-Yield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-hydroxy-6-methoxy-3-naphthoic acid (10 g, 0.045 moles) and thionyl chloride (6 g, 0.05 moles) are placed inside a 250 ml three-neck flask containing about 100 ml of methylene chloride. The mixture is stirred and brought to reflux under a nitrogen atmosphere. A catalytic amount of dimethylformamide is added. After about 20 minutes, all of the naphthoic acid is reacted and goes into solution. The solution is cooled to room temperature, and transferred to a 250 ml pressure equalizing funnel. The resulting 2-hydroxy-6-methoxy-3-napthoic acid chloride is then added to a 50 ml methylene chloride solution containing 5.6 g of aniline and 8 g of N,N-diethylaniline. The mixture is heated to reflux for about another 3 hours. After being cooled to room temperature, the mixture is filtered and washed with methanol, yielding 9.1 grams of a crude product after vacuum drying. The crude product is then purified by recrystallization from a mixture of dimethylformamide and methanol, affording 7.8 grams of a creamy while solid, 2-hydroxy-6-methoxy-3-naphthanilide (about 59%), having a melting point of 230° C. and an IR(KBr) of about 1640 cm-1 (amide C=O).

Workup

  1. temperatureto reflux under a nitrogen atmosphere
  2. temperatureThe mixture is heated
  3. temperatureto reflux for about another 3 hours
  4. temperatureAfter being cooled to room temperature
  5. filtrationthe mixture is filtered
  6. washwashed with methanol
  7. customyielding 9.1 grams of a crude product after vacuum
  8. customdrying
  9. customThe crude product is then purified by recrystallization from a mixture of dimethylformamide and methanol

Sources & evidence

ORD record
ord-66c25f400682424d9ac18c2ebfc0fa36
Source dataset
uspto-grants-1994_01
Patent number
US05281503

Reaction notes

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