Hydrochloric Acid → 6-cyano-1-methyl-1H-indole-2-carboxylic acid

HRID 2367731Notes

Reaction equation

HRID 2367731 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:17])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([C:15]#[N:16])[CH:9]=2)=[O:5])C.Cl>O1CCOCC1.O>[C:15]([C:10]1[CH:9]=[C:8]2[C:13]([CH:14]=[C:6]([C:4]([OH:5])=[O:3])[N:7]2[CH3:17])=[CH:12][CH:11]=1)#[N:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66656402Ethyl 6-cyano-1-methyl-1h-indole-2-carboxylate

Product 1

HCID 107980776-cyano-1-methyl-1H-indole-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 6-Cyano-1-methyl-1H-indole-2-carboxylic acid ethyl ester (51 mg, 0.22 mmol) in 1,4-dioxane/water (5:1, 6 mL) add LiOH monohydrate (13 mg, 0.31 mmol). Stir the reaction mixture at rt overnight. Remove the solvent in vacuo and dissolve the residue in water (2 mL) to form a solution. Acidify with 1 M HCl solution to form a white suspension. Collect the solid by filtration and dry to give the desired product 6-cyano-1-methyl-1H-indole-2-carboxylic acid as a solid (44 mg, 0.22 mmol).

Workup

  1. customRemove the solvent in vacuo
  2. dissolutiondissolve the residue in water (2 mL)
  3. customto form a solution
  4. customto form a white suspension
  5. customCollect the solid
  6. filtrationby filtration
  7. customdry

Sources & evidence

ORD record
ord-4bf89a8aa0d442b18e171b2b66a71076
Source dataset
uspto-grants-2014_04
Patent number
US08697911B2

Reaction notes

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