6-Methoxy-1,2,3,4-tetrahydroquinolin-2-one → 6-Methoxy-7-nitro-1,2,3,4-tetrahydroquinolin-2-one

HRID 1014375ノート

反応式

HRID 1014375 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7][CH2:6]2.[N:14]([O-:16])=[O:15].[Na+]>FC(F)(F)C(O)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:14]([O-:16])=[O:15])[NH:9][C:8](=[O:13])[CH2:7][CH2:6]2

参加物

5

反応物 2

HCID 108884676-Methoxy-1,2,3,4-tetrahydroquinolin-2-oneHCID 23668193Sodium Nitrite2 回

生成物 1

HCID 109440476-Methoxy-7-nitro-1,2,3,4-tetrahydroquinolin-2-one収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

A solution of 6-(methyloxy)-3,4-dihydro-2(1H)-quinolinone (400 mg, 2.25 mmol, Precursor Chemicals) in trifluoroacetic acid (4 mL, Aldrich) was treated with sodium nitrite (156 mg, 2.26 mmol, added slowly in about 4 portions, Aldrich). The dark brown reaction was stirred for 1 h after which an aliquot was taken out, diluted with water and extracted with ethyl acetate. TLC analysis of the ethyl acetate layer revealed that starting material remained. More sodium nitrite (50 mg, 0.72 mmol) was added and the reaction stirred for another 2 h at which point some precipitation was observed in the reaction. The reaction was poured over ice and then extracted with ethyl acetate. The organic layer, which still had undissolved solids in it, was concentrated to give 6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-quinolinone (372 mg, 70%) as a white powder. 1H NMR (400 MHz, DMSO-d6) 5 ppm 2.45-2.49 (m, 2 H), 2.98 (t, J=7.5 Hz, 2 H), 3.88 (s, 3 H), 7.29 (s, 1 H), 7.38 (s, 1 H), 10.18 (bs, 1 H).

後処理

  1. additionadded slowly in about 4 portions, Aldrich)
  2. customThe dark brown reaction
  3. extractionextracted with ethyl acetate
  4. stirringthe reaction stirred for another 2 h at which point
  5. customsome precipitation
  6. customwas observed in the reaction
  7. additionThe reaction was poured over ice
  8. extractionextracted with ethyl acetate
  9. concentrationThe organic layer, which still had undissolved solids in it, was concentrated

出典と根拠

ORDレコード
ord-25fbadf95ff24b2086c0b77c90cd7046
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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