Quinoline → 2-Amino-4-hydroxybenzonitrile

HRID 249970Notes

Reaction equation

HRID 249970 reaction equation
[NH2:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][C:5](C(O)=O)=[C:4]([OH:13])[CH:3]=1.N1C2C(=CC=CC=2)C=CC=1>[OH-].[Na+]>[NH2:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[CH:9][C:10]=1[C:11]#[N:12]

Participants

4

Reactant 2

HCID 7047QuinolineHCID 125651974-Amino-5-cyano-2-hydroxybenzoic acid

Product 1

HCID 124686832-Amino-4-hydroxybenzonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
160 °C

Procedure

4-Amino-5-cyano-2-hydroxybenzoic acid (2.1 g, 11.79 mmol) is added to a quinoline solution already heated to 160° C. (12 ml) and the reaction solution is stirred at 180° C. for a further hour. After cooling, it is diluted with about 50 ml of a 1N sodium hydroxide solution. The mixture is extracted with dichloromethane. Subsequently, the aqueous phase is adjusted to pH 6.5 with hydrochloric acid and extracted with ethyl acetate and methanol (as a solubilizer). The combined organic phases are dried over sodium sulphate. The desired product is obtained after concentrating the solvents in 76% yield (1.2 g).

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture is extracted with dichloromethane
  3. extractionextracted with ethyl acetate and methanol (as a solubilizer)
  4. dry with materialThe combined organic phases are dried over sodium sulphate

Sources & evidence

ORD record
ord-e578144a584348bbb5b70702975cc969
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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