Diethyl Ether → HCID 178451749, compound

HRID 1514179Notes

Reaction equation

HRID 1514179 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:9][CH2:8][C:7]=2[CH:20]=1)#[N:2].Cl.[NH2:22][OH:23].C(=O)(O)[O-].[Na+].CCOCC>C(O)C>[OH:23][NH:22][C:1](=[NH:2])[C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:10][CH2:9][CH2:8][C:7]=2[CH:20]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 68470153HCID 68470153, compound

Product 1

HCID 178451749HCID 178451749, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

1,1-Dimethylethyl 7-cyano-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carboxylate (Preparation 4) (350 mg, 1.285 mmol), hydroxylamine hydrochloride (223 mg, 3.21 mmol) and sodium bicarbonate (540 mg, 6.43 mmol) were suspended in ethanol (15 ml) and stirred at 55° C. for 5 hours. The reaction mixture was left standing overnight. LC/MS showed a single major product. Inorganics were removed by filtration, washing well with 10% MeOH/DCM to dissolve any precipitated product. Solvent evaporation yielded a white solid. Trituration with ether gave the title compound (320 mg). MS (ES) C16H23N3O3 requires 305; found 306.2 (M+H)+.

Workup

  1. waitThe reaction mixture was left
  2. waitstanding overnight
  3. customInorganics were removed by filtration
  4. washwashing well with 10% MeOH/DCM
  5. dissolutionto dissolve any precipitated product
  6. customSolvent evaporation
  7. customyielded a white solid

Sources & evidence

ORD record
ord-98b1026ee71e44abb8345e9be51f2ade
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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