Acetic Anhydride → HCID 67298129, compound

HRID 1520398Notes

Reaction equation

HRID 1520398 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[N:6]=[C:5]2[NH2:18].[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[N:6]=[C:5]2[NH:18][C:19](=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67298020HCID 67298020, compound

Product 1

HCID 67298129HCID 67298129, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A 100 mL round bottom flask was fitted with a reflux condenser and charged with 6-bromo-2-(pyridin-3-yl)quinazolin-4-amine (2.45 g, 8.14 mmol), acetic anhydride (5.81 g, 57.0 mmol) and acetic acid (30 mL). The reaction mixture was stirred at 90° C. for 20 min and then cooled to room temperature. A precipitate formed during the reaction and was collected by filtration and washed with water (100 mL). The solid was dried at 60° C. to give N-(6-bromo-2-(pyridin-3-yl)quinazolin-4-yl)acetamide as a white powder (1.83 g, 66%). 1H NMR (300 MHz, CDCl3) δ 9.72 (s, 1H), 8.84-8.69 (m, 3H), 8.22 (s, 1H), 8.02-7.90 (m, 2H), 7.53-7.41 (m, 1H), 2.83 (s, 3H).

Workup

  1. customA 100 mL round bottom flask was fitted with a reflux condenser
  2. temperaturecooled to room temperature
  3. customA precipitate formed during the reaction
  4. filtrationwas collected by filtration
  5. washwashed with water (100 mL)
  6. customThe solid was dried at 60° C.

Sources & evidence

ORD record
ord-a9b73c7b4b054bbcb394c0ee399d83bf
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

Loading…