3-Chloroaniline → HCID 57840790, compound

HRID 733700Notes

Reaction equation

HRID 733700 reaction equation
C(OC([N:8]1[C:12]2[C:13](Cl)=[N:14][CH:15]=[C:16]([C:17]([OH:19])=[O:18])[C:11]=2[C:10]([CH3:21])=[CH:9]1)=O)(C)(C)C.[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>O1CCOCC1.CCOC(C)=O.[OH-].[Na+]>[Cl:22][C:23]1[CH:24]=[C:25]([NH:26][C:13]2[C:12]3[NH:8][CH:9]=[C:10]([CH3:21])[C:11]=3[C:16]([C:17]([OH:19])=[O:18])=[CH:15][N:14]=2)[CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 2

HCID 79323-ChloroanilineHCID 44475513HCID 44475513, compound

Product 1

HCID 57840790HCID 57840790, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 7-chloro-3-methyl-pyrrolo[2,3-c]pyridine-1,4-dicarboxylic acid 1-tert-butyl ester (200 mg) and 3-chloroaniline (0.68 ml) in 1,4-dioxane (3 ml) was heated at 110° C. for 16 hours. The reaction mixture was diluted with EtOAc and basified with 1M NaOH, the aqueous layer was extracted and acidified to pH1 using 1M HCl to afford a precipitate. The precipitate was filtered off and washed with water until neutral. The solid was then sucked dry and dried over sodium hydroxide at 50° C. under vacuum to afford the title compound (197 mg).

Workup

  1. extractionthe aqueous layer was extracted
  2. customto afford a precipitate
  3. filtrationThe precipitate was filtered off
  4. washwashed with water until neutral
  5. customThe solid was then sucked dry
  6. dry with materialdried over sodium hydroxide at 50° C. under vacuum

Sources & evidence

ORD record
ord-9fd97d5317ac4436ab1825db6b1e5fdd
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

Loading…