Ammonium Hydroxide → Methyl indoline-2-carboxylate

HRID 6228

Reaction equation

HRID 6228 reaction equation
[Mg].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([O:13][CH2:14]C)=[O:12].[OH-].[NH4+]>CO>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 73125Ethyl indole-2-carboxylateHCID 5462224Magnesium2×

Product 1

HCID 2794655Methyl indoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Magnesium turnings (3.60 g) are added to a mixture of ethyl indole-2-carboxylate (I, Aldrich Chemical, 13.963 g) in methanol (200 ml). After evolution of gas has started, the mixture is placed in an ice bath and the temperature kept below 45°. After 4.5 hours all of the magnesium is used up and the temperature is 7°. At this time the mixture is added to ice cold hydrochloric acid (3N, 120 ml). The acidic mixture is then made alkaline (pH 10) with ammonium hydroxide (3N). The mixture is then extracted with methylene chloride (3 x). The combined organic layers are dried over magnesium sulfate and concentrated to give the title compound.

Workup

  1. customthe mixture is placed in an ice bath
  2. customkept below 45°
  3. customis 7°
  4. extractionThe mixture is then extracted with methylene chloride (3 x)
  5. dry with materialThe combined organic layers are dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aed351363b3f4779b0e84261ee5bce75
Source dataset
uspto-grants-1993_09
Patent number
US05247090

Linked notes

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