Glycol monoethyl ether → 4-(3-Hydroxymethyl-2-methylphenylamino)-6,7-dimethoxyquinoline-3-carbonitrile

HRID 1935135노트

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HRID 1935135 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[NH2:18][C:19]1[C:20]([CH3:27])=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][OH:23].Cl.N1C=CC=CC=1.C(OCCO)C>>[OH:23][CH2:22][C:21]1[C:20]([CH3:27])=[C:19]([NH:18][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]#[N:17])[CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 4

HCID 8076Glycol monoethyl etherHCID 577175(3-Amino-2-methylphenyl)methanolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

생성물 1

HCID 224665804-(3-Hydroxymethyl-2-methylphenylamino)-6,7-dimethoxyquinoline-3-carbonitrile수율 91.6%

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온도
139 °C

실험 절차

A mixture of 0.248 g (1 mmol)of 4-chloro-6,7-dimethoxy-quinoline-3-carbonitrile, 0.151 g (1.1 mmol) of 3-amino-2-methylbenzyl alcohol, 0.116 g (1 mmol) pyridine hydrochloride and 12 ml of 2-ethoxyethanol was heated in a 138-140° C. oil bath for 6 hours; progress of the reaction was monitored by TLC. When TLC indicated the disappearance of starting material, the reaction was cooled and concentrated in vacuo to a thick oil. To this oil was added 50 ml of water followed by 5 ml of 1M NaHCO3, approximately pH 8. The resulting precipitate was collected, washed with water and diethyl ether, and dried in vacuo at 65° C. to give 0.32 g (91.5%) of the desired product as light tan crystals. MP 123-125° C.;: mass spectrum (electrospray, m/e,): 349.9(M+H)+.

후처리

  1. temperaturethe reaction was cooled
  2. concentrationconcentrated in vacuo to a thick oil
  3. additionTo this oil was added 50 ml of water
  4. customThe resulting precipitate was collected
  5. washwashed with water and diethyl ether
  6. customdried in vacuo at 65° C.

출처 및 근거

ORD 기록
ord-6ee170aa84154a799f6dcb9bd5c81ca3
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384051B1

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