4-Chlorobenzylamine → HCID 178522935, compound

HRID 2299280Notes

Reaction equation

HRID 2299280 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]2[S:13][CH:14]=[CH:15][C:3]=12.[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH:22][C:8]([C:7]2[C:2]([OH:1])=[C:3]3[CH:15]=[CH:14][S:13][C:4]3=[N:5][CH:6]=2)=[O:10])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469713HCID 178469713, compound

Product 1

HCID 178522935HCID 178522935, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of ethyl 4-hydroxythieno[2,3-b]pyridine-5-carboxylate (J. Heterocyclic Chem. 1977, 14, 807) (0.447 g) and 4-chlorobenzylamine (2.43 mL) is stirred at 190° C. for 1 h. The reaction is then allowed to cool to rt and is diluted with toluene (5 mL). The resulting precipitate is filtered off and washed with toluene followed by hexanes to yield an off-white solid. This material is recrystallized from acetic acid/water then ethanol to yield 0.285 g (45%) of the title compound as a white solid.

Workup

  1. temperatureto cool to rt
  2. filtrationThe resulting precipitate is filtered off
  3. washwashed with toluene
  4. customto yield an off-white solid
  5. customThis material is recrystallized from acetic acid/water

Sources & evidence

ORD record
ord-788596f3c758482a8d203807eb9a5133
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

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