Hydrochloric Acid → 1-(7-Amino-5-bromoindolin-1-yl)ethanone

HRID 4927

Reaction equation

HRID 4927 reaction equation
C(O)C.[C:4]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([Br:19])=[CH:13][C:14]=2[N+:16]([O-])=O)[CH2:9][CH2:8]1)(=[O:6])[CH3:5].Cl>[Fe].O>[C:4]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([Br:19])=[CH:13][C:14]=2[NH2:16])[CH2:9][CH2:8]1)(=[O:6])[CH3:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27292431-Acetyl-5-bromo-7-nitroindoline

Product 1

HCID 197113381-(7-Amino-5-bromoindolin-1-yl)ethanoneYield 32.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a mixed solution of ethanol (400 ml) and water (100 ml), were added N-acetyl-5-bromo-7-nitroindoline (133.1 g), iron powder (10 mesh; 75 g) and concentrated hydrochloric acid (5 ml), and the mixture was subjected to refluxing for 5 hours with vigorous stirring. The reaction mixture was filtered by suction while hot to remove insoluble matter, and then the filtrate thereof was concentrated and cooled on standing to give the intended compound 38.3 g (32.2%) as a brown needle crystal. M.P.: 154°-155° C.

Workup

  1. temperatureto refluxing for 5 hours with vigorous stirring
  2. filtrationThe reaction mixture was filtered by suction while hot
  3. customto remove insoluble matter
  4. concentrationthe filtrate thereof was concentrated
  5. temperaturecooled

Sources & evidence

ORD record
ord-fa8c1a5973204abeab956b536c71aec8
Source dataset
uspto-grants-1993_09
Patent number
US05242912

Linked notes

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