Ethyl Acetate → 6-azido-N',5-dihydroxy-5,6,7,8-tetrahydronaphthalene-2-carboximidamide

HRID 470588Notes

Reaction equation

HRID 470588 reaction equation
[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[CH:10]=[C:9]([C:14]#[N:15])[CH:8]=[CH:7][C:6]=2[CH:5]1[OH:16])=[N+:2]=[N-:3].Cl.[NH2:18][OH:19].C(=O)(O)[O-].[Na+].CCOC(C)=O>CC(O)C>[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[CH:10]=[C:9]([C:14](=[N:18][OH:19])[NH2:15])[CH:8]=[CH:7][C:6]=2[CH:5]1[OH:16])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 131731135racemic (5S*,6R*)-6-azido-5-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 1317311366-azido-N',5-dihydroxy-5,6,7,8-tetrahydronaphthalene-2-carboximidamideYield 96%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Racemic (5S*,6R*)-6-azido-5-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (400 mg, 1.9 mmol) and hydroxylamine hydrochloride (260 mg, 3.7 mmol) were mixed in 2-propanol (7.5 mL). To this suspended solution was added sodium bicarbonate (627 mg, 7.5 mmol) and the solution was heated at reflux for 2 hr. Then the reaction mixture was cooled to room temperature and diluted by EtOAc (50 mL) and washed with water and brine. The combined aqueous layers were extracted again by EtOAc. The combined organic layers were dried (MgSO4) and concentrated to afford pure racemic (5S*,6R*,E/Z)-6-azido-N′,5-dihydroxy-5,6,7,8-tetrahydronaphthalene-2-carboximidamide (445 mg, 1.8 mmol, 96% yield).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 2 hr
  3. washwashed with water and brine
  4. extractionThe combined aqueous layers were extracted again by EtOAc
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cab8c872f4db4f4b85a7f5bfcb66b74d
Source dataset
uspto-grants-2014_01
Patent number
US08629282B2

Reaction notes

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