Methyl iodide → 7-amino-4-methyl-2H-1,4-benzoxazine

HRID 970652ノート

反応式

HRID 970652 の反応式
[C:1](=O)([O-])[O-].[K+].[K+].CI.[N+:9]([C:12]1[CH:13]=[CH:14][C:15]2[NH:20][CH2:19][CH2:18][O:17][C:16]=2[CH:21]=1)([O-])=O.[H-].[Na+]>CN(C=O)C>[CH3:1][N:20]1[CH2:19][CH2:18][O:17][C:16]2[CH:21]=[C:12]([NH2:9])[CH:13]=[CH:14][C:15]1=2

参加物

6

反応物 4

HCID 6328Methyl iodide2 回HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 184161517-Nitro-3,4-dihydro-2H-1,4-benzoxazine

生成物 1

HCID 112174297-amino-4-methyl-2H-1,4-benzoxazine収率 95.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Potassium carbonate (800 mg, 6 mmol) and methyl iodide (1.3 g, 9 mmol) were added to a solution of 3,4-dihydro-7-nitro-2H-benzo[b][1,4]oxazine (540 mg, 3 mmol) in DMF (10 mL). The reaction mixture was stirred at room temperature overnight. Sodium hydride (100 mg, 95%) and methyl iodide (1.0 g) were added and the reaction mixture was stirred at room temperature overnight. The solvent was removed under vacuum and the residue was suspended in water. A solid precipitated which was filtered and washed with water. The bright yellow solid was then suspended in MeOH (20 mL) and Pd/C (10%) was added. The suspension was stirred under an atmosphere of hydrogen overnight, then filtered through celite and the filtrate concentrated under vacuum to give the product (470 mg) as a purple oil.

後処理

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe solvent was removed under vacuum
  3. customA solid precipitated which
  4. filtrationwas filtered
  5. washwashed with water
  6. additionPd/C (10%) was added
  7. stirringThe suspension was stirred under an atmosphere of hydrogen overnight
  8. filtrationfiltered through celite
  9. concentrationthe filtrate concentrated under vacuum

出典と根拠

ORDレコード
ord-f1839c26ae8f4e118a78db9a98a785ef
出典データセット
uspto-grants-2007_12
特許番号
US07312233B2

反応ノート

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