Ammonia → 4-bromo-1H-indole-2-carboxamide

HRID 2365160Notes

Reaction equation

HRID 2365160 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[C:11]([C:17]([OH:19])=O)[NH:12]2.[NH3:20]>C(Cl)Cl>[Br:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[C:11]([C:17]([NH2:20])=[O:19])[NH:12]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 40426044-bromo-1H-indole-2-carboxylic acid

Product 1

HCID 591512734-bromo-1H-indole-2-carboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.9 mL, 10 mmol) was added to a suspension of 4-bromo-1H-indole-2-carboxylic acid (2.1 g, 8.8 mmol) in DCM and the mixture was stirred for 2 h. The solution formed was added drop-wise to a stirring mixture of ammonia (37%, 50 mL) and ice (50 mL). The resulting mixture was allowed to stand for 3 days. The mixture was filtered and the filtrate extracted with EtOAc. The solid from the filtration was dissolved in EtOAc and the organic solutions were combined, dried (MgSO4) and then evaporated to afford the title compound as a brown solid (2.1 g, 100%).

Workup

  1. customThe solution formed
  2. additionwas added drop-wise
  3. waitto stand for 3 days
  4. filtrationThe mixture was filtered
  5. extractionthe filtrate extracted with EtOAc
  6. filtrationThe solid from the filtration
  7. dissolutionwas dissolved in EtOAc
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-59c60a2e25634da18f36736045ed4cfe
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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