Ammonium Chloride → HCID 58118555, compound

HRID 1182850Notes

Reaction equation

HRID 1182850 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[C:4]=1[NH:11][CH2:12][C:13]([NH2:15])=[O:14].[NH4+].[Cl-]>CC(O)C>[NH2:10][C:9]1[C:5]2[C:4](=[C:3]([Br:2])[CH:8]=[CH:7][CH:6]=2)[NH:11][C:12]=1[C:13]([NH2:15])=[O:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 66864166HCID 66864166, compound

Product 1

HCID 58118555HCID 58118555, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

1.17 g (50.9 mmol) sodium was dissolved in 150 ml 2-propanol. Then, 10.82 g (42.6 mmol) 2-(2-bromo-6-cyano-phenylamino)acetamide was added and the solution was refluxed for 15 min. Thereafter, the reaction mixture was cooled to 0° C. and saturated NH4Cl solution was added. The solvent was concentrated, the resulting precipitate was sucked off and washed with water. 8.6 g (79%) 3-amino-7-bromo-1H-indole-2-carboxylic acid amide was obtained. ESI-MS [m/z]: 254, 256 [M+H]+

Workup

  1. temperaturethe solution was refluxed for 15 min
  2. concentrationThe solvent was concentrated
  3. washwashed with water

Sources & evidence

ORD record
ord-9cb455f558d049af9bf991a3ddac2882
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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