Hydrogen Bromide → HCID 68705832, compound

HRID 222121Notes

Reaction equation

HRID 222121 reaction equation
[BrH:1].[CH2:2]([O:4][C:5](=[O:20])[CH:6]([C:18]#[N:19])[CH:7]1[CH2:16][CH2:15][C:14]2[CH:13]=[N:12][CH:11]=[CH:10][C:9]=2[C:8]1=O)[CH3:3]>C(O)(=O)C.C(OCC)C>[BrH:1].[CH2:2]([O:4][C:5]([C:6]1[C:7]2[CH2:16][CH2:15][C:14]3[CH:13]=[N:12][CH:11]=[CH:10][C:9]=3[C:8]=2[NH:19][C:18]=1[Br:1])=[O:20])[CH3:3]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 68711116HCID 68711116, compound

Product 1

HCID 68705832HCID 68705832, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To stirred, cold (4° C.) 33% HBr in acetic acid (27 mL), cyano-(5-oxo-5,6,7,8-tetrahydro-isoquinolin-6-yl)-acetic acid ethyl ester 8C (7 mmol), dissolved in acetic acid (22 mL) and diethyl ether (22 mL), was added dropwise. The mixture was stirred at rt for 15 h. The yellow precipitate was filtered and repeatedly washed with diethyl ether affording the title product in 89% yield. ESI (+) MS: m/z 322 (MH+). 1H NMR: 1.32 (t, J=7.19, 3H), 3.02-3.33 (m, 4H), 4.17-4.31 (m, 2H), 7.89 (d, J=6.22, 1H), 8.61-8.64 (m, 1H), 8.65-8.70 (m, 1H), 13.49 (bs, 1H).

Workup

  1. stirringThe mixture was stirred at rt for 15 h
  2. filtrationThe yellow precipitate was filtered
  3. washrepeatedly washed with diethyl ether affording the title product in 89% yield

Sources & evidence

ORD record
ord-7fcf8e8ccafa4dbba96f9546a3639457
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

Loading…