Hydrochloric Acid → HCID 17803204, compound

HRID 2352508Notes

Reaction equation

HRID 2352508 reaction equation
C([BH3-])#N.[Na+].[N:5](=[C:7]([C:9]([CH3:20])([CH3:19])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH3:8])[OH:6].[ClH:21].CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2>CO>[ClH:21].[F:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][C:9]([CH3:19])([CH3:20])[CH:7]([NH:5][OH:6])[CH3:8])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6451Bromocresol GreenHCID 5003444Sodium cyanoborohydrideHCID 73655415HCID 73655415, compound

Product 1

HCID 17803204HCID 17803204, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

19.6 g (0.29 mol) of sodium cyanoborohydride (95%) are added in portions to a solution of 66.8 g (0.29 mol) of 2-hydroximino-3,3-dimethyl-4-(4-fluorophenoxy)-butane in 500 ml of methanol, which is kept at pH 3 with concentrated hydrochloric acid against bromocresol green. When the addition has ended, the pH value is kept at 3 with hydrochloric acid for a further 3 hours and the mixture is then subsequently stirred at room temperature for 16 hours. The reaction mixture is acidified to pH 1 and concentrated in vacuo. The residue is taken up in chloroform/water, the organic phase is separated off and dried over sodium sulphate and the solvent is distilled off in vacuo. 52.3 g (67.1% of theory) of 4-(4-fluorophenoxy)-3,3-dimethyl-2-butyl-hydroxylamine hydrochloride of melting point 99° C. are obtained. ##STR95##

Workup

  1. additionWhen the addition
  2. concentrationconcentrated in vacuo
  3. customthe organic phase is separated off
  4. dry with materialdried over sodium sulphate
  5. distillationthe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-779b1c16c59e4fb1b07c4c58ca6abd2a
Source dataset
uspto-grants-1989_10
Patent number
US04877786

Reaction notes

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