Glycol monoethyl ether → HCID 22466580, compound

HRID 612226

Reaction equation

HRID 612226 reaction equation
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

Participants

5

Reactant 4

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

Product 1

HCID 22466580HCID 22466580, compoundYield 91.6%

Conditions

Temperature
139 °C

Procedure

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)+.

Workup

  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.

Sources & evidence

ORD record
ord-fe96da2993f14102af2bb15ec19db7f1
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Linked notes

Loading…