Water → 1,4-Dihydrocinnoline

HRID 1924401Notes

Reaction equation

HRID 1924401 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](C(OC)=O)=[CH:3][N:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(Cl)Cl>C(OCC)C>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 13958988Methyl cinnoline-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 124272971,4-Dihydrocinnoline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.00 g of methyl cinnolin-4-carboxylate in 15 ml diethyl ether is added dropwise at 0° C. to a suspension of 222 mg of lithium aluminium hydride in 5 ml of diethyl ether. After 1.5 hours water is carefully added dropwise to the reaction mixture, this is stirred with methylene chloride and suction filtered through a glass fibre filter. The aqueous phase is extracted with methylene chloride and the combined organic phases are dried over magnesium sulphate and evaporated down. According to 1H-NMR a mixture of cinnoline and 1,4-dihydro-cinnoline compound is obtained as a yellow oil which is reacted further without any more purification.

Workup

  1. filtrationfiltered through a glass fibre filter
  2. extractionThe aqueous phase is extracted with methylene chloride
  3. dry with materialthe combined organic phases are dried over magnesium sulphate
  4. customevaporated down
  5. additiona mixture of cinnoline

Sources & evidence

ORD record
ord-369abbc5366747ca81a4009cf0ac2b7c
Source dataset
uspto-grants-2012_05
Patent number
US08178541B2

Reaction notes

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