Hydroxylamine → N-(1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)-N'-hydroxyterephthalamide

HRID 2076428Notes

Reaction equation

HRID 2076428 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:26]=[CH:25][C:7]([C:8]([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:17]([CH3:22])([CH3:21])[CH2:16][CH2:15][C:14]([CH3:24])([CH3:23])[C:13]=3[CH:12]=2)=[O:9])=[CH:6][CH:5]=1.[NH2:28][OH:29]>CO>[CH3:21][C:17]1([CH3:22])[C:18]2[C:13](=[CH:12][C:11]([NH:10][C:8](=[O:9])[C:7]3[CH:6]=[CH:5][C:4]([C:3]([NH:28][OH:29])=[O:2])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[C:14]([CH3:24])([CH3:23])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 13632689Methyl 4-((5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-YL)carbamoyl)benzoate

Product 1

HCID 11440001N-(1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)-N'-hydroxyterephthalamideYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-terephthalamic acid methyl ester 7 (0.20 g, 0.55 mmol) in MeOH (2 mL) was added an hydroxylamine solution (1.76 M, 2 mL) in MeOH and the reaction mixture was stirred 1 h at room temperature under magnetic stirring. The reaction mixture was adjusted to pH=5, concentrated and the residue was partitioned between EtOAc and H2O. The organic layer was dried with Na2SO4 and the product was crystallized by dissolving the mixture at 80° C. in CH3CN to give N-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)-N′-hydroxyterephthalamide EHT 7706 (0.05 g, 25% yield) as a white solid.

Workup

  1. concentrationconcentrated
  2. customthe residue was partitioned between EtOAc and H2O
  3. dry with materialThe organic layer was dried with Na2SO4
  4. customthe product was crystallized
  5. dissolutionby dissolving the mixture at 80° C. in CH3CN

Sources & evidence

ORD record
ord-549e14151237439c9f5e8ccbaf145a89
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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