Ammonium Chloride → 6-Amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

HRID 519206ノート

反応式

HRID 519206 の反応式
[CH3:1][CH:2]1[N:15]2[C:6]([CH2:7][O:8][C:9]3[C:14]2=[CH:13][C:12]([N+:16]([O-])=O)=[CH:11][CH:10]=3)=[N:5][NH:4][C:3]1=[O:19].[Cl-].[NH4+]>CO.[Zn]>[NH2:16][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][C:6]1[N:15]2[CH:2]([CH3:1])[C:3](=[O:19])[NH:4][N:5]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 86727620HCID 86727620、化合物

生成物 1

HCID 867272916-Amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one収率 77%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

To a solution of 4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (10 g, 38.2 mmol) and ammonium chloride (20.5 g, 382.0 mmol) in MeOH (200 mL) was added zinc powder (24.8 g, 382.0 mol) and the resulting mixture was stirred for 24 h at 25° C. The reaction mixture was filtered and the filtrate was washed with methanol (5×30 mL). The filtrate was combined and concentrated in vacuo and the residue was purified by chromatography on silica gel (eluting with 10% MeOH in DCM) to give 6-amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (6.8 g, 77%) as a yellow solid. 1H NMR (DMSO-d6, 400 MHz): δ 10.72 (s, 1H), 6.67 (d, J=8.4 Hz, 1H), 6.42 (d, J=2.4 Hz, 1H), 6.15 (q, J=8.4 Hz, J=2.4 Hz, 1H), 4.82 (brs, 2H), 4.52 (q, J=6.4 Hz, 1H), 4.43 (d, J=12.8 Hz, 2H), 1.30 (d, =6.4 Hz, 3H).

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with methanol (5×30 mL)
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by chromatography on silica gel (eluting with 10% MeOH in DCM)

出典と根拠

ORDレコード
ord-1457538487044c2b895bf9f8594cbef6
出典データセット
uspto-grants-2015_08
特許番号
US09115151B2

反応ノート

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