Hydrochloric Acid → 7,8,9-Trimethoxy-2,3-methylenedioxy-11H-indeno[1,2-c]isoquinoline Hydrochloride

HRID 505358ノート

反応式

HRID 505358 の反応式
[CH2:1]1[O:17][C:16]2[CH:15]=[CH:14][C:5]([CH2:6][NH:7][CH2:8][CH:9](OC)OC)=[CH:4][C:3]=2[O:2]1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH:23]=O.[ClH:32].[NH4+].[OH-]>FC(F)(F)C(O)=O.CO.O.CC(C)=O.CCOCC>[ClH:32].[CH3:18][O:19][C:20]1[C:21]2[C:8]3[N:7]=[CH:6][C:5]4[C:14]([C:9]=3[CH2:23][C:22]=2[CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])=[CH:15][C:16]1[O:17][CH2:1][O:2][C:3]=1[CH:4]=4

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 68583,4,5-TrimethoxybenzaldehydeHCID 14923Ammonium HydroxideHCID 11459077HCID 11459077、化合物

生成物 1

HCID 113037737,8,9-Trimethoxy-2,3-methylenedioxy-11H-indeno[1,2-c]isoquinoline Hydrochloride収率 45%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6422Trifluoroacetic acid溶媒HCID 86590524Methanol water acetone溶媒

反応条件

温度
100 °C

実験手順

Amine 12b (2.28 g, 9.52 mmol) and 3,4,5-trimethoxybenzaldehyde (10c, 3.77 g, 19.2 mmol) were reacted in trifluoracetic acid (25 mL) with stirring at 100° C. for 3 h. The reaction mixture was cooled and hydrochloric acid (2 M in ether, 10 mL) and ether (200 mL) were added. The precipitate was isolated and dissolved in methanol-water-acetone 1:1:1 (250 mL) and NH4OH was used to bring the mixture to a basic pH. The mixture was extracted with chloroform (350 mL). The organic layer was washed with brine (200 mL), dried (Na2SO4) and concentrated. The residue was dissolved in chloroform (60 mL) and hydrochloric acid (2 M in dry ether, 10 mL) was added. The precipitate was collected and washed with hot methanol (10 mL) and ether 20 (mL) to provide a yellow hygroscopic solid (1.65 g, 45%), mp 257-259° C. 1H NMR (300 MHz, CD3OD) δ 9.04 (s, 1H), 7.63 (s, 1H), 7.51 (s, 1H), 7.18 (s, 1H), 6.32 (s, 2H), 4.28 (3H), 4.25 (2H), 3.98 (3H), 3.90 (s, 3H); low resolution ESIMS m/z (rel intensity) 352 (MH+, 100). Anal. Calcd for C20H18NO5Cl(H2O)1.9: C, 56.92; H, 5.21; N, 3.32. Found: C, 56.92; H, 5.02; N, 3.29.

後処理

  1. temperatureThe reaction mixture was cooled
  2. customThe precipitate was isolated
  3. extractionThe mixture was extracted with chloroform (350 mL)
  4. washThe organic layer was washed with brine (200 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in chloroform (60 mL)
  8. additionhydrochloric acid (2 M in dry ether, 10 mL) was added
  9. customThe precipitate was collected
  10. washwashed with hot methanol (10 mL) and ether 20 (mL)

出典と根拠

ORDレコード
ord-5b53ab7972074465af44d49267c05d07
出典データセット
uspto-grants-2010_08
特許番号
US07781445B2

反応ノート

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