Hydrogen Bromide → 5-Bromo-2,3-dihydro-1H-inden-2-amine--hydrogen bromide (1/1)

HRID 540782Notes

Reaction equation

HRID 540782 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.[Br:12]Br.[BrH:14]>O>[BrH:12].[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Br:14])[CH:9]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 1227642-Aminoindan hydrochloride

Product 1

HCID 121920575-Bromo-2,3-dihydro-1H-inden-2-amine--hydrogen bromide (1/1)Yield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-amino-2,3-dihydro-1H-indene hydrochloride salt (10.0 g, 58.9 mmol) in water (50 mL) was warmed to 60° C. Next, bromine was added dropwise (3.50 mL, 67.9 mmol) over a 50 min period. Stirred for 1 hour, cooled to RT, stirred 1 hour, treated with 5 mL of 48% HBr (aq) and filtered. The residue was dried in a vacuum oven overnight (40° C.) to give 2-amino-5-bromo-2,3-dihydro-1H-indene hydrobromide salt (14.5 g, 84% yield) as a single isomer: 1H NMR (600 MHz, DMSO-d6) δ 8.08 (br s, 3H), 7.47 (s, 1H), 7.35 (dd, J=7.9, 0.9 Hz, 1H), 7.21 (d, J=7.9 Hz, 1H), 3.97 (br s, 1H), 3.18-3.26 (m, 2H), 2.85-2.94 (m, 2H).

Workup

  1. stirringstirred 1 hour
  2. filtrationfiltered
  3. customThe residue was dried in a vacuum oven overnight (40° C.)

Sources & evidence

ORD record
ord-180b2d0ebda14c38bd5c66d558403448
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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