Citric Acid → HCID 58306856, compound

HRID 1909905Notes

Reaction equation

HRID 1909905 reaction equation
[NH2:1][C:2]1[C:9]([C:10]#[CH:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Br:12].C(NC(=O)[O-])(C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN1CCCC1=O>[Br:12][C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[C:9]2[C:2]=1[NH:1][CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 311Citric AcidHCID 21252905Tert-butylcarbamateHCID 58307094HCID 58307094, compound

Product 1

HCID 58306856HCID 58306856, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of 4-amino-3-bromo-5-ethynylbenzonitrile (0.57 g) and 1-methyl-2-pyrrolidinone (12 mL) was added tert-butylcarbamate (0.57 g) under ice-cooling, followed by stirring at room temperature for 24 hours. To the reaction mixture was added a 10% aqueous citric acid solution under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to obtain 7-bromo-1H-indole-5-carbonitrile (0.55 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-44e17cbf87c3412f95f762ac29c88cdb
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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