Sodium Hydroxide → HCID 44242581、化合物

HRID 1775960ノート

反応式

HRID 1775960 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14]CC)=[O:13])[C:6]1[CH2:17][N:18]([CH3:21])[CH2:19][CH2:20][C:5]2=1.[OH-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]1[CH2:17][N:18]([CH3:21])[CH2:19][CH2:20][C:5]2=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 57930381HCID 57930381、化合物

生成物 1

HCID 44242581HCID 44242581、化合物収率 21.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

Ethyl 2-(6-chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetate (0.3 g, 2.9 mmol) in THF (10 mL) was added to a solution of sodium hydroxide (0.177 g, 2.9 mmol) in water (3 mL) and heated at 75° C. for 1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was removed; water (10 mL) was added to the residue and the aqueous layer was washed with ethyl acetate (2×10 mL). The pH of aqueous layer was adjusted to 2-3, and the aqueous layer was washed with ethyl acetate. The aqueous layer was evaporated, the residue was extracted with methanol, filtered, the filtrate was concentrated under reduced pressure to yield 2-(6-chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetic acid (175 mg). 1H NMR (CD3OD): 7.50 (s, 1H) 7.30 (d, 1H), 7.10 (d, 1H), 5.1 (d, 1H), 5.0 (d, 1H), 4.4 (s, 2H), 4.2 (m, 1H), 4.0 (m, 1H), 3.4 (s, 3H), 3.2 (m, 2H).

後処理

  1. customAfter completion of the reaction
  2. customthe solvent was removed
  3. additionwater (10 mL) was added to the residue
  4. washthe aqueous layer was washed with ethyl acetate (2×10 mL)
  5. washthe aqueous layer was washed with ethyl acetate
  6. customThe aqueous layer was evaporated
  7. extractionthe residue was extracted with methanol
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-d66e3aa2fcb040de9d3fcd39aeed533b
出典データセット
uspto-grants-2016_02
特許番号
US09260429B2

反応ノート

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