Hydroxylamine → HCID 11222341, compound

HRID 2076423Notes

Reaction equation

HRID 2076423 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([NH:16][C:17]3[CH:26]=[CH:25][C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2.[NH2:28][OH:29]>CO>[OH:29][NH:28][C:21]([C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:14]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:27])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=3[CH:7]=2)=[O:15])=[CH:26][CH:25]=1)=[O:22]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 13655816HCID 13655816, compound

Product 1

HCID 11222341HCID 11222341, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoate 3 (0.200 g, 0.5 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 RT 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-(4-(hydroxycarbamoyl)phenyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamide EHT 3741 (0.070 g, 35% yield) as a pale red 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-e002d19708174c05b7d5624708617ab4
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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