Hydroxyamine hydrochloride → HCID 178426596, compound

HRID 1673240Notes

Reaction equation

HRID 1673240 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:15]=[C:14]2[O:16][C:17]([CH3:28])([CH3:27])[CH2:18][CH:19]([NH:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C:13]2=[CH:12][C:11]=1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1.Cl.[NH2:37][OH:38].C([O-])(O)=O.[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([NH:37][OH:38])=[NH:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:15]=[C:14]2[O:16][C:17]([CH3:27])([CH3:28])[CH2:18][CH:19]([NH:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:23])[CH3:24])[C:13]2=[CH:12][C:11]=1[C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 24993727HCID 24993727, compound

Product 1

HCID 178426596HCID 178426596, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 317 (120 mg, 0.24 mmol), hydroxylamine hydrochloride (65.6 mg, 0.94 mmol), and NaHCO3 (119 mg, 1.42 mmol) in 10 mL of EtOH was refluxed for 16 h. The reaction mixture was partitioned between brine (50 mL) and CH2Cl2 (50 mL). The aq layer was separated and extracted with CH2Cl2 (2×50 mL). The organic layers were combined, dried over MgSO4, and concentrated to give the product, which was taken into the next step without further purification.

Workup

  1. customThe reaction mixture was partitioned between brine (50 mL) and CH2Cl2 (50 mL)
  2. customThe aq layer was separated
  3. extractionextracted with CH2Cl2 (2×50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give the product, which
  7. customwas taken into the next step without further purification

Sources & evidence

ORD record
ord-d4dddd04677a44cfb2b3464f6c2964e9
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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