Sodium Hydroxide → 4-[(3-Chlorophenyl)amino]-1-ethyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid

HRID 733746Notes

Reaction equation

HRID 733746 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]3[CH:15]=[CH:16][N:17]([CH2:18][CH3:19])[C:13]=3[C:12]([C:20]([O:22]CC)=[O:21])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]3[CH:15]=[CH:16][N:17]([CH2:18][CH3:19])[C:13]=3[C:12]([C:20]([OH:22])=[O:21])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57840969Ethyl 4-[(3-chlorophenyl)amino]-1-ethyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

Product 1

HCID 578410324-[(3-Chlorophenyl)amino]-1-ethyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acidYield 13.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 4-[(3-chlorophenyl)amino]-1-ethyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (0.160 g) and 2M sodium hydroxide (0.5 ml) in methanol (1.5 ml) was irradiated at 120° C. for 3 minutes with microwaves. The solvent was evaporated and the residue partitioned between ethyl acetate and water. The aqueous layer was removed, acidified to pH1 and extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to afford the title compound as a white oil (0.020 g).

Workup

  1. customwas irradiated at 120° C. for 3 minutes with microwaves
  2. customThe solvent was evaporated
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe aqueous layer was removed
  5. extractionextracted with ethyl acetate three times
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-5a0da96d13cc4f2a86ae25d2042c6e02
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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