Ethyl 5-cyanoindole-2-carboxylate → 5-Aminomethyl-1H-indole-2-carboxylic acid ethyl ester

HRID 843998Notes

Reaction equation

HRID 843998 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]#[N:16])=[CH:10][CH:9]=2)=[O:5])[CH3:2]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][NH2:16])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 4714953Ethyl 5-cyanoindole-2-carboxylate

Product 1

HCID 252537375-Aminomethyl-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-Cyano-1H-indole-2carboxylic acid ethyl ester (1.8 grams, 8.4 mmole) and Bu4N+BH3− in methylene chloride (80 ml) was refluxed for 4 hours. The mixture was concentrated to a brown oil which was dissolved in 10% hydrochloric acid (50 ml) and refluxed for 1 hour. The mixture was extracted with ethyl acetate (discarded) and the pH was neutralized. The aqueous was extracted with ethyl acetate. The combined extracts were dried over Na2SO4, filtered, and concentrated to give a solid. (0.920 g). MW 218.258; MS (m/e) 218 (M+).

Workup

  1. concentrationThe mixture was concentrated to a brown oil which
  2. dissolutionwas dissolved in 10% hydrochloric acid (50 ml)
  3. temperaturerefluxed for 1 hour
  4. extractionThe mixture was extracted with ethyl acetate (discarded)
  5. extractionThe aqueous was extracted with ethyl acetate
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a solid

Sources & evidence

ORD record
ord-92f6329b118840dd893056102cb4afaf
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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