Hydrochloric Acid → N-(1-Methyl-1H-indole-2-carbonyl)glycine

HRID 362482Notes

Reaction equation

HRID 362482 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][NH:5][C:6]([C:8]1[N:9]([CH3:17])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7].[OH-].[Li+].Cl>O1CCOCC1>[CH3:17][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:8]1[C:6]([NH:5][CH2:4][C:3]([OH:18])=[O:2])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 23435401HCID 23435401, compound

Product 1

HCID 51052332N-(1-Methyl-1H-indole-2-carbonyl)glycineYield 93.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(1-Methylindole-2-carbonyl)glycine methyl ester (1.687 g, 6.85 mmol) was dissolved in 1,4-dioxane (10 mL) and was treated with 1N lithium hydroxide (7.0 mL, aq) with stirring. The reaction mixture turned clear immediately and was acidified with 1N HCl and concentrated to remove 1,4-dioxane to result in a purple precipitate. The precipitate was filtered, washed with water, and dried in vacuo to give the title product as a purple powder (1.482 g, 93%). TLC: (methylene chloride:methanol:acetic acid, 20:1:1, silica gel): Rf =0.28; 1H NMR (CD3OD): δ 7.61 (dt, J=8.2, 1H). 7.44 (dd, J=8.5, 0.8, 1H), 7.32-7.26 (m, 1H), 7.13-7.09 (m, 1H), 7.04 (s, 1H), 4.08 (s, 2H), 3.99 (s, 3H).

Workup

  1. concentrationconcentrated
  2. customto remove 1,4-dioxane
  3. customto result in a purple precipitate
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-276f34dcc2e44856861fa1708836f57a
Source dataset
uspto-grants-1999_02
Patent number
US05869519

Reaction notes

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