Hydroxyamine hydrochloride → HCID 178428722, compound

HRID 2059936Notes

Reaction equation

HRID 2059936 reaction equation
[C:1]([C:3]1[C:4]([CH3:20])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH2:6]2)#[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:4]([CH3:20])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 516892Sodium Bicarbonate2×HCID 54756912tert-Butyl 6-cyano-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 178428722HCID 178428722, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,1-Dimethylethyl 6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 16; 404 mg; 1.48 mmol) was stirred overnight at 80° C. with hydroxylamine hydrochloride (619 mg; 8.90 mmol) and sodium bicarbonate (748 mg; 8.9 mmol) in ethanol (10 ml). Further sodium bicarbonate (400 mg) and hydroxylamine hydrochloride (300 mg) were added, and heating continued for ca. 8 h. The mixture was cooled to room temperature, and the resulting solid removed, washed with ethanol, and dried under high vacuum to give the title compound as a white solid (431 mg).

Workup

  1. temperatureheating
  2. customthe resulting solid removed
  3. washwashed with ethanol
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-1ce2497d29d7489986cfb874f9b21088
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

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