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

HRID 1859596Notes

Reaction equation

HRID 1859596 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 1 N 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-94248197516e4376800f56b44ecdf4dc
Source dataset
uspto-grants-2003_03
Patent number
US06528506B2

Reaction notes

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