Hydrochloric Acid → HCID 19009242, compound

HRID 1742487Notes

Reaction equation

HRID 1742487 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:15])[C:5]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.Cl>CO>[Cl:3][C:4]1[C:5]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[C:6]([OH:15])[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 132594022-Chloro-3-(4-nitrophenoxy)naphthalene-1,4-dione

Product 1

HCID 19009242HCID 19009242, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of sodium borohydride was added, whilst ice-cooling, to a solution of 11 g of 3-chloro-2-(4-nitrophenoxy)-1,4-naphthoquinone (prepared as described in Preparation 17) in 150 ml of methanol, and the mixture was stirred, whilst ice-cooling, for 30 minutes. The mixture was then poured into a mixture of ice and 15 ml of 2N aqueous hydrochloric acid to give a precipitate, which was collected by filtration, washed with water and dried under reduced pressure in the presence of phosphorus pentoxide, to give 9 g of 3-chloro-1,4-dihydroxy-2-(4-nitrophenoxy)naphthalene.

Workup

  1. temperaturecooling, for 30 minutes
  2. customto give a precipitate, which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. dry with materialdried under reduced pressure in the presence of phosphorus pentoxide

Sources & evidence

ORD record
ord-cfc7f86c64de434095c731e35c577213
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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