Sodium Hydroxide → HCID 25222870, compound

HRID 499753Notes

Reaction equation

HRID 499753 reaction equation
[Sn](Cl)Cl.[N+:4]([C:7]1[CH:8]=[C:9]([CH:24]=[CH:25][CH:26]=1)[O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)([O-])=O.[OH-].[Na+]>CO>[C:15]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[CH:17][C:12]([CH2:11][O:10][C:9]2[CH:8]=[C:7]([CH:26]=[CH:25][CH:24]=2)[NH2:4])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 165692534-(3-Nitro-phenoxymethyl)-biphenyl

Product 1

HCID 25222870HCID 25222870, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tin (II) chloride (13.6 g (60 mmole)) is added to a solution of 4-(3-Nitro-phenoxymethyl)-biphenyl (4.6 g, 15 mmole) in 120 ml methanol. The reaction mixture is refluxed for 12 hr. The reaction is cooled to room temperature, 4 N of NaOH solution is added with stirring to adjust pH=8. The resulting mixture is filtered through a plug of CELITE, the filtrate concentrated and taken up in ethyl acetate. The organic layer is washed with brine and dried over Na2SO4, and concentrated. The resulting solid is washed with little methanol to yield 3-(Biphenyl-4-ylmethoxy)-aniline as a yellow solid. MS: 276(M+1).

Workup

  1. temperatureThe reaction mixture is refluxed for 12 hr
  2. filtrationThe resulting mixture is filtered through a plug of CELITE
  3. concentrationthe filtrate concentrated
  4. washThe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. washThe resulting solid is washed with little methanol

Sources & evidence

ORD record
ord-a5ab6f21168e4291b24eb93ea28bfc41
Source dataset
uspto-grants-2010_08
Patent number
US07767706B2

Reaction notes

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