Hydrogen Bromide → 1-(4-Carboxyphenyl)-2-cyanoindole

HRID 1769200Notes

Reaction equation

HRID 1769200 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[C:15]2[C:23]#[N:24])=[CH:10][CH:9]=1)=[O:7])(C)(C)C.Br>C(O)(=O)C>[C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[C:15]2[C:23]#[N:24])=[CH:10][CH:9]=1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 103360241-[4-(Tert-butoxycarbonyl)phenyl]-2-cyanoindole

Product 1

HCID 104004611-(4-Carboxyphenyl)-2-cyanoindoleYield 97.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3.6 g (0.011 mol) of 1-[4-(tert-butoxycarbonyl)phenyl]-2-cyanoindole was dissolved in 40 ml of acetic acid and 10 ml of 30% hydrogen bromide in acetic acid was added dropwise. After stirring for 10 minutes, the slurry was poured onto 200 g of ice-water, and the resulting precipitate was filtered, washed with water and air-dried, to give 2.8 g (0.0107 mol) of 1-(4-carboxyphenyl)-2-cyanoindole, m.p., 128°-131° C.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water
  3. customair-dried

Sources & evidence

ORD record
ord-8cb1db2af9824cad9a3ef7e3f61cae94
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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