Hydrochloric Acid → HCID 74041496, compound

HRID 1380313Notes

Reaction equation

HRID 1380313 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21](=[O:24])[CH2:22][CH3:23])=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:12]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[N:27](OCCC(C)C)=[O:28]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21](=[O:24])[C:22](=[N:27][OH:28])[CH3:23])=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:12]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 23326420HCID 23326420, compound

Product 1

HCID 74041496HCID 74041496, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Benzyloxyethyl)-2-oxo-6-propionyl-1,2,3,4-tetrahydroquinoline (32.4 g) was dissolved in methylene chloride (97 ml) and the solution was saturated with hydrogen chloride. To the stirred solution was added dropwise iso-amyl nitrite (13.5 g) over 0.5 hour. After stirring for 1 hour, the reaction mixture was evaporated in vacuo and the oily residue was dissolved in diethyl ether and extracted with 10% aqueous solution of sodium hydroxide. The extract was washed with diethyl ether, acidified with diluted hydrochloric acid, and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was triturated with benzene to give 1-(2-benzyloxyethyl)-6-(2-hydroxyiminopropionyl)-2-oxo-1,2,3,4-tetrahydroquinoline (9.19 g).

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. dissolutionthe oily residue was dissolved in diethyl ether
  3. extractionextracted with 10% aqueous solution of sodium hydroxide
  4. washThe extract was washed with diethyl ether
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe oily residue was triturated with benzene

Sources & evidence

ORD record
ord-8c46b18d9c5f4e0b887515ebb6119fb7
Source dataset
uspto-grants-1986_04
Patent number
US04581356

Reaction notes

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