Hydrochloric Acid → (2,5-Dimethyl-1H-indol-1-yl)acetic acid

HRID 1374794Notes

Reaction equation

HRID 1374794 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH3:13])=[CH:8][CH:7]=2.Br[CH2:15][C:16]([O:18]CC)=[O:17].[OH-].[Na+].Cl>CN(C=O)C.CCO>[CH3:3][C:4]1[N:5]([CH2:15][C:16]([OH:18])=[O:17])[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH3:13])=[CH:8][CH:7]=2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 709652,5-Dimethyl-1H-indole

Product 1

HCID 18735250(2,5-Dimethyl-1H-indol-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

60% sodium hydride/oil (0.64 g) was added to a solution of 2,5-dimethyl-1H-indole (2.0 g) in DMF (15 ml). After 15 min ethyl bromoacetate (2.7 ml) was added quickly and the reaction stirred for 20 min. The reaction mixture was quenched with 1% aqueous acetic acid (100 ml), extracted with ethyl acetate (2×100 ml) and washed with water (2×50 ml) and brine (20 ml). The extracts were dried (MgSO4), filtered and evaporated in vacuo to yield a brown solid. The solid was dissolved in EtOH (20 ml) and aqueous sodium hydroxide (1M,10 ml) added. After 1 hour the solution was adjusted to pH6 with aqueous hydrochloric acid (1M,˜10 ml), and then evaporated in vacuo. The residue was purified by flash column chromatography (gradient 1–10% methanol in dichloromethane). The sub-title compound was obtained as a red/brown solid (1.3 g).

Workup

  1. customThe reaction mixture was quenched with 1% aqueous acetic acid (100 ml)
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washwashed with water (2×50 ml) and brine (20 ml)
  4. dry with materialThe extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto yield a brown solid
  8. customevaporated in vacuo
  9. customThe residue was purified by flash column chromatography (gradient 1–10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b5698180b3d84ad6880bd1917c42f5b0
Source dataset
uspto-grants-2007_01
Patent number
US07166607B2

Reaction notes

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