Hydrochloric Acid → HCID 68586587, compound

HRID 659817Notes

Reaction equation

HRID 659817 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([N+:19]([O-])=O)=[C:14]([CH3:22])[CH:13]=1.O.O.[Sn](Cl)Cl.Cl>CO>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([NH2:19])=[C:14]([CH3:22])[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 68586237HCID 68586237, compound

Product 1

HCID 68586587HCID 68586587, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 15.00 g (46.9 mmol) of 4-(5,6,7,8-tetrahydro-2-naphthoxy)-2,5-dimethylnitrobenzene in 60 ml of methanol is admixed first of all with 31.8 g (140.7 mmol) of tin(II) chloride dihydrate at room temperature and then slowly, with ice cooling, with 60 ml of concentrated hydrochloric acid. The reaction mixture is refluxed for 2 h, cooled to room temperature, concentrated and admixed with water and the residue is isolated by filtration and dried under reduced pressure (15.3 g, 86% purity, 99.5% yield, log P (pH 2.3)=3.08).

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture is refluxed for 2 h
  3. concentrationconcentrated
  4. customthe residue is isolated by filtration
  5. customdried under reduced pressure (15.3 g, 86% purity, 99.5% yield, log P (pH 2.3)=3.08)

Sources & evidence

ORD record
ord-e222d5fbb59845cab897d3bc70c6a3eb
Source dataset
uspto-grants-2011_12
Patent number
US08080688B2

Reaction notes

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