Lithium Hydroxide → 6-Chloro-4-(isopropylamino)nicotinic acid

HRID 595459

反応式

HRID 595459 の反応式
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH:14]2[CH2:17]C[CH2:15]2)[C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][N:3]=1.[Li+].[OH-]>C(O)C.O>[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH:14]([CH3:17])[CH3:15])[C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 89689654Ethyl 6-chloro-4-(cyclobutylamino)nicotinate

生成物 1

HCID 896898576-Chloro-4-(isopropylamino)nicotinic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

Ethyl 6-chloro-4-(cyclobutylamino)nicotinate (2) (3 g, 12.3 mmol) in ethanol (20 mL) and water (10 mL) was stirred at rt. LiOH (61.7 mmol, 5 equiv.) was added and the reaction mixture was stirred at room temperature for 4 h. The solvent was concentrated under reduced pressure. Diluted with EtOAc and added water. The aqueous layer was collected and acidified to pH 3-4 using solid citric acid. Solid material precipitated out. Filtered the solid material and dried under vacuum to furnish the title compound (3). 1H NMR: 400 MHz, DMSO-d6: δ 1.20 (d, J=6.40 Hz, 6H), 3.80-3.88 (m, 1H), 6.80 (s, 1H), 8.20 (d, J=7.60 Hz, 1H), 8.51 (s, 1H), 13.33 (bs, 1H).

後処理

  1. concentrationThe solvent was concentrated under reduced pressure
  2. additionDiluted with EtOAc
  3. additionadded water
  4. customThe aqueous layer was collected
  5. customSolid material precipitated out
  6. filtrationFiltered the solid material
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-6d97c22430b04337b204542e287b2196
出典データセット
uspto-grants-2016_01
特許番号
US09242976B2

関連ノート

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