Cyanogen Bromide → HCID 68571396, compound

HRID 655266Notes

Reaction equation

HRID 655266 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]([NH:15][NH2:16])=[O:14])=[CH:7][CH:6]=2.[N:17]#[C:18]Br>CO.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]1[O:14][C:18]([NH2:17])=[N:16][N:15]=1)=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 57742331HCID 57742331, compound

Product 1

HCID 68571396HCID 68571396, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of (3-bromo-quinolin-6-yl)-acetic acid hydrazide (prepared according to procedure described herein) (4.12 g, 14.7 mmol), cyanogen bromide (1.1 eq., 16.2 mmol, 1.7 g) and KHCO3 (1.25 eq., 18.3 mmol, 1.83 g) was stirred in methanol (30 mL) at ambient temperature for 18 hours. The was then diluted with water (40 mL) and the solid was collected via filtration and washed with cold methanol and dried to return the title compound as an off white solid (4.02 g, 13.2 mmol, 90%). 1H NMR (DMSO-d6): δ 4.27 (2H, s), 6.94 (s, 2H), 7.71 (dd, 1H), 7.86 (d, 1H), 8.02 (d, 1H), 8.73 (d, 1H); 8.93 (d, 1H); MS (m/z) 305 [M+H+]+.

Workup

  1. filtrationthe solid was collected via filtration
  2. washwashed with cold methanol
  3. customdried

Sources & evidence

ORD record
ord-b6dd3c3860b64c2580cd3720479d9329
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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