1-Bromooctane → HCID 121312908, compound

HRID 523373Notes

Reaction equation

HRID 523373 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:14]([O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([NH2:1])[CH:11]=[CH:10]2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 4286056-Amino-2-naphthalenol

Product 1

HCID 121312908HCID 121312908, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

3 grams (g) (18.85 millimoles (mmol)) of 6-aminonaphthalene-2-ol is dissolved in 100 milliliters (mL) of acetone, and 4 g (20.7 mmol) of 1-bromooctane and 13.0 g (94.2 mmol) of potassium carbonate (K2CO3) are added thereto. The reaction mixture is stirred under reflux at 60° C. for 24 hours, and cooled down to room temperature (25° C.). The obtained reaction mixture is concentrated, and purified by silica gel column chromatography (n-hexane:EtOAc=3:1 volume ratio), to give 4.5 g (16.6 mmol) of 6-octyloxynaphthalene-2-amine. The yield is 88%.

Workup

  1. temperaturecooled down to room temperature (25° C.)
  2. customThe obtained reaction mixture
  3. concentrationis concentrated
  4. custompurified by silica gel column chromatography (n-hexane:EtOAc=3:1 volume ratio)

Sources & evidence

ORD record
ord-6f8628b1d1bb4ff28939780e39f8f782
Source dataset
uspto-grants-2016_05
Patent number
US09335442B1

Reaction notes

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