Hydrochloric Acid → alpha-Amino-7-ethyl-1H-indole-3-acetic Acid Ethyl Ester

HRID 1253283Notes

Reaction equation

HRID 1253283 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5](=[N:17]O)[C:6]1[C:14]2[C:9](=[C:10]([CH2:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[CH3:2].Cl>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([NH2:17])[C:6]1[C:14]2[C:9](=[C:10]([CH2:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136393701HCID 136393701, compound

Product 1

HCID 14010221alpha-Amino-7-ethyl-1H-indole-3-acetic Acid Ethyl Ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 7-ethyl-α-(hydroxyimino)-1H-indole-3-acetic acid ethyl ester 5 (7.3 g, 0.028 mol) in ethanol (200 mL) was added concentrated HCl (3 mL) and 10% Pd/C (1.0 g). The mixture was hydrogenated at 40 p.s.i. for 4 hours at 22° C. The catalyst and the solvent were removed and the residue was dissolved in water. After washing with methylene chloride, the aqueous phase was basified with 20% sodium hydroxide. The precipitated product, α-amino-7-ethyl-1H-indole-3-acetic acid ethyl ester 6 (6.0 g, 87%), was filtered, washed with water and dried. A sample recrystallized from hot ethanol had m.p. 120°-122° C.

Workup

  1. customThe catalyst and the solvent were removed
  2. dissolutionthe residue was dissolved in water
  3. washAfter washing with methylene chloride
  4. filtrationThe precipitated product, α-amino-7-ethyl-1H-indole-3-acetic acid ethyl ester 6 (6.0 g, 87%), was filtered
  5. washwashed with water
  6. customdried
  7. customA sample recrystallized from hot ethanol

Sources & evidence

ORD record
ord-ad2061946ae448249d101ab39a4cd046
Source dataset
uspto-grants-1988_05
Patent number
US04748252

Reaction notes

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