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

HRID 519206노트

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HRID 519206 반응식
[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

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 86727620HCID 86727620, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

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온도
25 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1457538487044c2b895bf9f8594cbef6
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115151B2

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