Hydrochloric Acid → 5-amino-6-bromo-1-indanone

HRID 1451539Notes

Reaction equation

HRID 1451539 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:14])[C:10](=[O:15])[CH2:9][CH2:8]2)(=O)C.Cl>[OH-].[Na+]>[NH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:14])[C:10](=[O:15])[CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9993147N-(6-Bromo-1-oxo-2,3-dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 103987765-amino-6-bromo-1-indanone

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5-acetylamino-6-bromo-1-indanone (36.0 g, 0.13 mol) and 6M aqueous hydrochloric acid (800 mL) was refluxed for 1 h. The homogenous solution was then cooled to 0° C. and adjusted to pH 8 with 10M aqueous NaOH (~480 mL). The precipitate formed was collected, washed with water and dried under vacuum to afford 30.0 g (quantitative) of the title compound as a light brown powder. 1H NMR (acetone-d6): δ7.65 (1H, s), 6.90 (1H, s), 5.80 (2H, br s), 2.95 (2H, t), 2.50 (2H, t).

Workup

  1. temperaturewas refluxed for 1 h
  2. customThe precipitate formed
  3. customwas collected
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-713ca051392c483aa80e8380c9e15be7
Source dataset
uspto-grants-1997_02
Patent number
US05604260

Reaction notes

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