Hydroxyamine hydrochloride → HCID 178513252, compound

HRID 1807571Notes

Reaction equation

HRID 1807571 reaction equation
[OH:1][C@@H:2]1[CH2:11][CH2:10][CH2:9][C:8]2[C:7]([C:12]#[N:13])=[CH:6][CH:5]=[CH:4][C:3]1=2.Cl.[NH2:15][OH:16].C(=O)(O)[O-].[Na+]>CCO>[OH:16][NH:15][C:12]([C:7]1[C:8]2[CH2:9][CH2:10][CH2:11][C@@H:2]([OH:1])[C:3]=2[CH:4]=[CH:5][CH:6]=1)=[NH:13]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 58355020(R)-5-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Product 1

HCID 178513252HCID 178513252, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Prepared using General Procedure 1. To a stirring solution of (R)-5-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carbonitrile INT-2 (79.1 mg, 0.46 mmol) in EtOH (2 not) was added hydroxylamine hydrochloride (34.9 mg, 0.50 mmol) and sodium bicarbonate (42.2 mg, 0.50 mmol). The mixture was heated at 70° C. for 18 h. The product was purified by chromatography (MeOH/DCM) to provide 27.3 mg (29%) (R)-N,5-dihydroxy-5,6,7,8-tetrahydronaphthalene-1-carboximidamide INT-4 as a white solid. LCMS-ESI (m/z) calculated for C11H11NO: 173.2; found 174.1 [M+H]+, 156.1 [M−NH4]+, tR=2.60 min. (S)-N,5-dihydroxy-5,6,7,8-tetrahydronaphthalene-1-carboximidamide INT-5 was prepared in an analogous fashion from (S)-5-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carbonitrile INT-3.

Workup

  1. customPrepared
  2. customThe product was purified by chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-61e05bf109df4de6bc6d3ba2f4fa60f5
Source dataset
uspto-grants-2013_01
Patent number
US08357706B2

Reaction notes

Loading…