Water → Ethyl 2-(4-acetamido-2-methyl-1H-indol-1-yl)acetate

HRID 505932Notes

Reaction equation

HRID 505932 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:17])[N:6]2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26].O>C(OCC)(=O)C>[C:25]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:17])[N:6]2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59431293Ethyl 2-(4-amino-2-methyl-1H-indol-1-yl)acetate

Product 1

HCID 59431286Ethyl 2-(4-acetamido-2-methyl-1H-indol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The (4-amino-2-methyl-1H-indol-1-yl)-acetic acid, ethyl ester prepared above (8.59 g) was dissolved in ethyl acetate (175 ml) then triethylamine (5.2 ml, 37 mmol) added followed by acetyl chloride (2.6 ml, 37 mmol). An exotherm to 35° C. was observed and a thick suspension resulted. After stirring for 4 hours during which the mixture was allowed to cool back to ambient temperature, water (85 ml) was added and the ethyl acetate removed by evaporation under vacuum. The solid was collected by filtration, washed with water (25 ml) followed by 50% v/v aqueous acetonitrile (50 ml) then dried in a vacuum oven at 50° C. overnight to provide (4-acetylamino-2-methyl-1H-indol-1-yl)-acetic acid, ethyl ester, as an off-white solid, 7.26 g (77% from (4-nitro-2-methyl-1H-indol-1-yl)-acetic acid, ethyl ester).

Workup

  1. customto 35° C.
  2. customa thick suspension resulted
  3. customthe ethyl acetate removed by evaporation under vacuum
  4. filtrationThe solid was collected by filtration
  5. washwashed with water (25 ml)
  6. customthen dried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-195fe3b3803a4ef99d10bab4ca000e5c
Source dataset
uspto-grants-2010_08
Patent number
US07781598B2

Reaction notes

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