O-Toluidine → Methaqualone

HRID 1729641

反応式

HRID 1729641 の反応式
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])O[C:2]2=O.C(OC(=O)C)(=O)C.[CH3:20][C:21]1OC(=O)[C:24]2[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=2[N:22]=1.NC1C(C)=CC=CC=1>CC1C=CC=CC=1C>[CH3:20][C:21]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=2[CH3:2])[C:5](=[O:12])[C:31]2[C:23](=[CH:24][CH:28]=[CH:29][CH:30]=2)[N:22]=1

参加物

6

反応物 4

HCID 7242O-ToluidineHCID 7918Acetic AnhydrideHCID 8359Isatoic AnhydrideHCID 68236Acetanthranil

生成物 1

HCID 6292Methaqualone収率 64%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒2 回

実験手順

The isatoic anhydride and acetic anhydride were reacted under the condition described for the preparation of 2-methyl-4H-3,1-benzoxazine-4-one. The pyridine was distilled from the reaction mixture under reduced pressure. The crude reaction product was taken up in 100 ml of o-xylene and placed in a 200 ml one-necked flask equipped with a Dean-Stark trap and a reflux condenser. The o-toluidine was added to the xylene solution. The reaction mixture was heated to reflux for 4 hours. 1.8 ml of water was collected in the Dean-Stark trap. The xylene was removed from the reaction product by distillation under reduced pressure. The resulting residue was crystallized twice from methanol to give 16 parts (64% yield) of 2-methyl-3-(o-tolyl)-quinazoline-4 (3H)-one with m.p. 113°-115° C. The reaction product was characterized by melting point, IR and NMR.

後処理

  1. distillationThe pyridine was distilled from the reaction mixture under reduced pressure
  2. customThe crude reaction product
  3. customplaced in a 200 ml one-necked flask
  4. customequipped with a Dean-Stark trap and a reflux condenser
  5. temperatureThe reaction mixture was heated
  6. temperatureto reflux for 4 hours
  7. custom1.8 ml of water was collected in the Dean-Stark trap
  8. customThe xylene was removed from the reaction product by distillation under reduced pressure
  9. customThe resulting residue was crystallized twice from methanol

出典と根拠

ORDレコード
ord-4e79fd1e4e6543018bae9e7379e09792
出典データセット
uspto-grants-1976_11
特許番号
US03989698

関連ノート

読み込み中…