Hydrazine hydrate (1:1) → HCID 57742338, compound

HRID 655267Notes

Reaction equation

HRID 655267 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]1O[C:16]([NH2:18])=[N:15][N:14]=1)=[CH:7][CH:6]=2.O.[NH2:20][NH2:21]>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[N:20]([NH2:21])[C:16]([NH2:18])=[N:15][N:14]=1)=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68571396HCID 68571396, compound

Product 1

HCID 57742338HCID 57742338, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 5-(3-bromo-quinolin-6-ylmethyl)-[1,3,4]oxadiazol-2-ylamine (3.53 g, 11.6 mmol), hydrazine hydrate (30 mL) and water (15 mL) was heated in a microwave vial at 170° C. and 2 bar of pressure for 1 hour. After cooling the formed solid was collected via filtration and washed with cold methanol and dried to return the title compound as white solid (1.79 g, 5.6 mmol, 49%). 1H NMR (DMSO-d6): δ 4.13 (2H, s), 5.46 (s, 2H), 5.56 (s, 2H), 7.23 (d, 1H), 7.81 (s, 1H), 7.98 (d, 1H), 8.71 (d, 1H); 8.91 (d, 1H); MS (m/z) 319 [M+H+]+.

Workup

  1. temperatureAfter cooling the formed solid
  2. filtrationwas collected via filtration
  3. washwashed with cold methanol
  4. customdried

Sources & evidence

ORD record
ord-7336576d2b214abb934b7c462e355763
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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