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

HRID 1198381ノート

反応式

HRID 1198381 の反応式
[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

参加物

9

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-66c25f400682424d9ac18c2ebfc0fa36
出典データセット
uspto-grants-1994_01
特許番号
US05281503

反応ノート

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