Indole-3-Butyric Acid → 4-[1-(3-Nitrobenzyl)indol-3-yl]butyric acid

HRID 1974563

Reaction equation

HRID 1974563 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4]1.[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br)([O-:20])=[O:19]>CN(C)C=O>[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4]1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 8617Indole-3-Butyric AcidHCID 24758Sodium hydrideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 191017574-[1-(3-Nitrobenzyl)indol-3-yl]butyric acidYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil) (0.59 g) in N,N-dimethylformamide (10 ml) was added a solution of 4-(3-indolyl)butyric acid (1.0 g) in N,N-dimethylformamide (5 ml). The mixture was stirred at room temperature for 30 minutes and cooled at -40° C. To the mixture was added a solution of 3-nitrobenzyl bromide (1.06 g) in N,N-dimethylformamide (5 ml). The mixture was stirred at -40° C. for 20 minutes and partitioned between ethyl acetate and 7% hydrochloric acid. The organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was washed with diisopropyl ether to give 4-[1-(3-nitrobenzyl)indol-3-yl]butyric acid as a white powder (1.20 g).

Workup

  1. temperaturecooled at -40° C
  2. stirringThe mixture was stirred at -40° C. for 20 minutes
  3. custompartitioned between ethyl acetate and 7% hydrochloric acid
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-02bfec7440644823a74f27c76fe0cd28
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Linked notes

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