Hydroxylamine → HCID 76787417, compound

HRID 2403221Notes

Reaction equation

HRID 2403221 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[NH2:22][OH:23]>CCO>[NH2:2][C:1](=[N:22][OH:23])[C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 66795480tert-butyl 3-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)propanoate

Product 1

HCID 76787417HCID 76787417, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 3-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)propanoate (11.85 g; 41.38 mmol; 1 eq.) was suspended in EtOH (237 mL). Hydroxylamine (6.1 mL; 206.90 mmol; 5 eq.) was added in one portion. The reaction mixture was stirred at RT for 48 h. The reaction mixture was concentrated under vacuum to give the title compound as a yellow oil. Diisopropyl ether (50 mL) was added. The resulting mixture was sonicated and concentrated under vacuum. This process was repeated 3 times, affording Intermediate 35 as a yellowish solid (13.2 g; quantitative). 1H NMR: (DMSO-d6, 400 MHz) δ 9.51 (br s, 1H), 7.43-7.34 (m, 2H), 7.09-7.06 (d, J=8.17 Hz, 1H), 5.71 (br s, 2H), 3.56 (s, 2H), 2.79-2.64 (m, 6H), 2.47-2.42 (t, J=6.93 Hz, 2H), 1.39 (s, 9H), traces of EtOH by NMR. HPLC/MS: 320.1.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-677b33f05830419ca966068dc5f91414
Source dataset
uspto-grants-2014_08
Patent number
US08802663B2

Reaction notes

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