Water → HCID 10294138, compound

HRID 131541Notes

Reaction equation

HRID 131541 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][C:12]([C:17]#[N:18])=[CH:11][CH:10]=2)=[O:5])[CH3:2].Cl.[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:24][NH2:25].C(N(C(C)C)CC)(C)C.O>C(O)CC>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:25][CH2:24][C:23]1[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:21]([Cl:20])[CH:22]=1)=[CH:13][C:12]([C:17]#[N:18])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27642873-Chloro-4-methoxybenzylamine hydrochlorideHCID 12069372HCID 12069372, compound

Product 1

HCID 10294138HCID 10294138, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To 10.0 g (38.4 mmol) 4-chloro-6-cyanoquinoline-3-carboxylic acid ethyl ester was added 10.4 g (50 mmol, 1.5 eq) 3-chloro-4-methoxybenzyl amine hydrochloride and 35 mL (228 mmol, 6 eq) diisopropylethylamine (Aldrich, 99.5+%). The mixture was dispersed in 200 mL n-propanol and brought to reflux for two hours. The solution was then poured into 500 mL water. The resulting precipitate was filtered, then washed with 500 mL water, then twice washed with 50 mL absolute ethanol to yield 14.87 g (37.6 mmol, 97% yield) of the title compound as a white fiberous solid after codistilling with absolute ethanol: mp: 161-162° C.; LC/MS (M/Z) 396 [M+H] observed, 97% purity.

Workup

  1. temperatureto reflux for two hours
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with 500 mL water
  4. washtwice washed with 50 mL absolute ethanol

Sources & evidence

ORD record
ord-f2d16f1663c64a2da8d0f1987c2b97e5
Source dataset
uspto-grants-2008_06
Patent number
US07384958B2

Reaction notes

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