2-Amino-2-methyl-1-propanol → 2-(5-Bromoindan-2-yl)-4,4-dimethyloxazoline

HRID 868012Notes

Reaction equation

HRID 868012 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([C:11]([OH:13])=O)[CH2:5]2.[NH2:14][C:15]([CH3:19])([CH3:18])[CH2:16]O>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([C:11]1[O:13][CH2:16][C:15]([CH3:19])([CH3:18])[N:14]=1)[CH2:5]2

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 219861245-bromo-2,3-dihydro-1H-indene-2-carboxylic acid

Product 1

HCID 212895082-(5-Bromoindan-2-yl)-4,4-dimethyloxazolineYield 63%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3.9 g of 5-bromo-2-indancarboxylic acid and 2 g of 2-amino-2-methyl-1-propanol were added to 100 ml of xylene. The mixture was heated under reflux for 24 hours while removing the water produced. The reaction mixture was concentrated in vacuo and 20 ml of water was added to the residue. The mixture was extracted with chloroform. The extract was washed with water, dried and then concentrated in vacuo. The residue was purified by silica gel column chromatography to give 3 g of 2-(5-bromoindan-2-yl)-4,4-dimethyloxazoline as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. customwhile removing the water
  4. customproduced
  5. concentrationThe reaction mixture was concentrated in vacuo and 20 ml of water
  6. additionwas added to the residue
  7. extractionThe mixture was extracted with chloroform
  8. washThe extract was washed with water
  9. customdried
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f60566a10b14404e8ddf99df88790e93
Source dataset
uspto-grants-1988_10
Patent number
US04777257

Reaction notes

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