Acetic Acid → 3-(Diethylamino)-5-methoxy-1H-indole-2-carboxamide, monohydrochloride

HRID 21592

Reaction equation

HRID 21592 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][C:5]=1[C:15](OCC)=[O:16])[CH3:2].[NH2-:22].[Li+].C(O)(=O)C.[ClH:28]>CCOCC>[ClH:28].[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][C:5]=1[C:15]([NH2:22])=[O:16])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 24532Lithium amideHCID 13837937ethyl 3-(diethylamino)-5-methoxy-1H-indole-2-carboxylate

Product 1

HCID 1317190223-(Diethylamino)-5-methoxy-1H-indole-2-carboxamide, monohydrochlorideYield 36%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared from ethyl 3-(diethylamino)-5-methoxy-1H-indole-2-carboxylate (Unangst PC, et al., J. Heterocyclic Chem. 1987;24:817) and lithium amide by the procedure described in Example 18, with the exception that dilute acetic acid is substituted for 1.0N HCl during the wash of the ethyl acetate extracts. The crude product is purified by flash chromatography (silica gel, 30% ethyl acetate in dichloromethane elution) to give a foam. The foam is dissolved in ether and treated with gaseous HCl to provide the product salt in 36% yield after recrystallization from acetonitrile; mp 244° C.-dec.

Workup

  1. washwash of the ethyl acetate
  2. customThe crude product is purified by flash chromatography (silica gel, 30% ethyl acetate in dichloromethane elution)
  3. customto give a foam
  4. customto provide the product salt in 36% yield
  5. customafter recrystallization from acetonitrile

Sources & evidence

ORD record
ord-37fa8988fca1478b905c4ec599fe19b5
Source dataset
uspto-grants-1995_06
Patent number
US05424329

Linked notes

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