Hydroxyamine hydrochloride → HCID 178451587, compound

HRID 1514185Notes

Reaction equation

HRID 1514185 reaction equation
[C:1]([C:3]1[C:13]2[CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:22][OH:23].C(=O)(O)[O-].[Na+]>C(O)C>[OH:23][NH:22][C:1](=[NH:2])[C:3]1[C:13]2[CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 575058801,1-Dimethylethyl 6-cyano-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 178451587HCID 178451587, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,1-dimethylethyl 6-cyano-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 14) (1.15 g), hydroxylamine hydrochloride (1.18 g) and sodium bicarbonate (1.76 g) were heated at 60° C. in ethanol (100 ml) for 18 hours under argon. The cooled reaction was evaporated to dryness, partitioned between DCM (100 ml) and water (100 ml). The DCM layer was collected and the water layer washed with DCM (50 ml). The combined DCM layers were dried and evaporated. The title compound (506 mg) was isolated by chromatography eluting with 5% methanol in DCM. δH (400 MHz, CDCl3) 7.27 (1H, s) 7.16-7.13 (2H, m), 5.38 (1H, br. s), 3.58-3.55 (4H, m), 3.05 (2H, br. s), 2.89 (2H, br. s) 1.46 (2H br. s), 1.12 (9H, br. s); MS (ES) C16H23N3O3 requires 305; found 306 [M+H]+.

Workup

  1. customThe cooled reaction
  2. customwas evaporated to dryness
  3. custompartitioned between DCM (100 ml) and water (100 ml)
  4. customThe DCM layer was collected
  5. washthe water layer washed with DCM (50 ml)
  6. dry with materialThe combined DCM layers were dried
  7. customevaporated

Sources & evidence

ORD record
ord-0b77e403bd324e24af27a3272db7ba0c
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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