Phosphorus oxychloride → 4-Chloro-7-methoxy-8-(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile

HRID 989358노트

반응식

HRID 989358 반응식
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:21]([O:22][CH3:23])=[CH:20][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:7]=2[CH:6]=1)[NH:14][CH:13]=[C:12]([C:17]#[N:18])[C:11]3=O.[Cl:24]CCOC1C(OC)=CC2C=C3C(C(=O)C(C#N)=CN3)=CC=2C=1.P(Cl)(Cl)(Cl)=O>CN(C)C=O>[Cl:24][C:11]1[C:10]2[C:15](=[CH:16][C:7]3[CH:6]=[C:5]([O:4][CH2:3][CH2:2][Cl:1])[C:21]([O:22][CH3:23])=[CH:20][C:8]=3[CH:9]=2)[N:14]=[CH:13][C:12]=1[C:17]#[N:18]

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 115372188-(2-Chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrileHCID 116384657-(2-Chloroethoxy)-8-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

생성물 1

HCID 115157734-Chloro-7-methoxy-8-(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile수율 87%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a slurry of 1.11 g of 8-(2-chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile and 7-(2-chloroethoxy)-8-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile (1:1 mixture) and 5 mL of phosphorus oxychloride is added 0.15 mL of anhydrous dimethylformamide. This is stirred and heated to reflux for 20 minutes using an oil bath, followed concentration in vacuo. The dark residue is quenched with 30 mL of cold water. The solid formed is collected, washed with water and dried to give 1.02 g (87%) of 4-chloro-7-methoxy-8(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile and 4-chloro-8-methoxy-7(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile (1:1 mixture) as a greenish yellow solid, m.p. 195-209° C. dec.

후처리

  1. temperatureheated
  2. temperatureto reflux for 20 minutes
  3. concentrationconcentration in vacuo
  4. customThe dark residue is quenched with 30 mL of cold water
  5. customThe solid formed
  6. customis collected
  7. washwashed with water
  8. customdried

출처 및 근거

ORD 기록
ord-f4d69c700e514154887c632f90bab6da
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06638929B2

반응 노트

불러오는 중…