Glycol monoethyl ether → HCID 22466768, compound

HRID 1935136Notes

Reaction equation

HRID 1935136 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].[CH2:18]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)[CH3:19].Cl.N1C=CC=CC=1.C(OCCO)C>>[CH2:18]([C:20]1[CH:26]=[CH:25][C:23]([NH:24][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:22][CH:21]=1)[CH3:19]

Participants

5

Reactant 4

HCID 8076Glycol monoethyl etherHCID 115044-EthylanilineHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 22466768HCID 22466768, compoundYield 97.5%

Conditions

Temperature
139 °C

Procedure

A mixture of 0.248 g (1 mmol)of 4-chloro-6,7-dimethoxy-quinoline-3-carbonitrile, 0.14 ml (1.1 mmol) of 4-ethylaniline, 0.116 g (1 mmol) pyridine hydrochloride and 12 ml of 2-ethoxyethanol was heated in a 138-140° C. oil bath for 1 hour; 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 0.325 g (97.5%) of the desired product as light cream crystals. MP 248-250° C.;: mass spectrum (electrospray, m/e,): 333.1462.

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-61b06f4566374313ab088a4ebf8badd6
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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