Hydrochloric Acid → HCID 20280494, compound

HRID 1247908Notes

Reaction equation

HRID 1247908 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([O:13][C:14]2[C:19]([Cl:20])=[CH:18][C:17]([N+:21]([O-])=O)=[CH:16][N:15]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>O1CCOCC1>[Cl:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([O:13][C:14]2[C:19]([Cl:20])=[CH:18][C:17]([NH2:21])=[CH:16][N:15]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13472411HCID 13472411, compound

Product 1

HCID 20280494HCID 20280494, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2.64 g. (11.7 mmol.) of stannous chloride in 2.4 ml. of concentrated hydrochloric acid and 1.75 ml. of p-dioxane at 50° was added 1.2 g. (3.54 mmol.) of 2-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3-chloro-5-nitropyridine. The resulting mixture was heated up to reflux for 0.5 hours, cooled, and poured into sodium hydroxide (pH 14) in cracked ice. This mixture was extracted twice with 150 ml. of methylene chloride. The combined organic layer was washed with water and brine. It was then dried (Na2SO4) and concentrated to give 1.0 g. (3.23 mmole) of light purple solid; mp. 129.8°-132.3°

Workup

  1. temperatureThe resulting mixture was heated up
  2. temperatureto reflux for 0.5 hours
  3. temperaturecooled
  4. extractionThis mixture was extracted twice with 150 ml
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialIt was then dried (Na2SO4)
  7. concentrationconcentrated
  8. customto give 1.0 g

Sources & evidence

ORD record
ord-e8b1ea244c9e4ab9a6de4d1298da610b
Source dataset
uspto-grants-1985_06
Patent number
US04521426

Reaction notes

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