Hydrochloric Acid → methyl 5-bromo-1H-indole-2-carboxylate

HRID 1760720Notes

Reaction equation

HRID 1760720 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.Cl.[CH3:15]O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH3:15])=[O:12])=[CH:5]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2521375-Bromo-1H-indole-2-carboxylic acid

Product 1

HCID 914343methyl 5-bromo-1H-indole-2-carboxylate

Procedure

A solution of 5-Bromo-1H-indole-2-carboxylic acid (commercial, 10.0 g, 41.6 mmol) in methanol (200 ml) was cooled to 0° C. and saturated with HCl(g). The resulting solution was allowed to warm gradually to room temperature overnight. The solvent was removed in vacuo and the residue treated with 0.88 ammonia (500 ml). The resulting solution was extracted with dichloromethane (3-fold 150 ml) and the combined organics dried (magnesium sulphate) and the solvent removed in vacuo to give the required product as a colourless oil (8.35 g).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue treated with 0.88 ammonia (500 ml)
  3. extractionThe resulting solution was extracted with dichloromethane (3-fold 150 ml)
  4. dry with materialthe combined organics dried (magnesium sulphate)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ffeb4d93a16c460886728a380c06e43f
Source dataset
uspto-grants-2005_01
Patent number
US06844362B2

Reaction notes

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