Quinoline → 2-Amino-4-hydroxy-3-methylbenzonitrile

HRID 407596Notes

Reaction equation

HRID 407596 reaction equation
[CH2:1]([N:8]1C(=O)C2=CC=CC=C2C1=O)CCCCC=C.[OH-:19].[Na+].[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=CC=1>>[NH2:21][C:30]1[C:25]([CH3:24])=[C:26]([OH:19])[CH:27]=[CH:28][C:29]=1[C:1]#[N:8]

Participants

4

Reactant 3

HCID 7047QuinolineHCID 14798Sodium HydroxideHCID 53236045N-(hept-6-enyl)phthalimide

Product 1

HCID 134647162-Amino-4-hydroxy-3-methylbenzonitrileYield 82%

Conditions

Temperature
170 °C

Procedure

A mixture of compound 75 (19 g, 0.1 mol) in quinoline (50 mL) was heated to 170° C. for 2 h (until effervescence ceased). The reaction mixture was cooled to RT and aqueous NaOH solution was added (1M, 500 mL) followed by pet. ether (500 mL). The reaction mixture was stirred for 15 min and the aqueous layer was separated. The aqueous layer was further washed with pet. ether (2×300 mL) to remove quinoline completely. The aqueous layer was acidified with 1.5N HCl to pH=5, the solid was filtered off and dried under vacuum. The obtained solid was further washed with 5% ethyl acetate in pet. ether to give pure title compound (12 g, 82%).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customthe aqueous layer was separated
  3. washThe aqueous layer was further washed with pet. ether (2×300 mL)
  4. customto remove quinoline completely
  5. filtrationthe solid was filtered off
  6. customdried under vacuum
  7. washThe obtained solid was further washed with 5% ethyl acetate in pet. ether

Sources & evidence

ORD record
ord-4040c5294c004dd394ec8a4c74333a12
Source dataset
uspto-grants-2014_06
Patent number
US08754106B2

Reaction notes

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