Sodium Hydroxide → 1-Amino-6-bromoisoquinoline

HRID 636911

反応式

HRID 636911 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](OC1C=CC=CC=1)=[N:7][CH:6]=[CH:5]2.C([O-])(=O)C.[NH4+:23].[OH-].[Na+]>>[NH2:23][C:8]1[C:9]2[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

参加物

4

反応物 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 226658626-Bromo-1-phenoxyisoquinoline

生成物 1

HCID 226076161-Amino-6-bromoisoquinoline収率 71.8%

反応条件

温度
150 °C

実験手順

A mixture of 12 g of 1c and 27 g of ammonium acetate was heated at 150° C. for 14 hours. After cooling to room temperature aqueous 3N NaOH was added and the mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with brine and aqueous 2N hydrochloric acid was added until pH2-3. The acid aqueous layer was separated, made basic (pH 10) with aqueous 2N NaOH and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried (MgSO4) and concentrated to give 6.4 g of 1d. 1H-NMR 200 MHz (CDCl3) δ: 5.1 (2H, br s), 6.96 (1H, dd, J=6 Hz and J=]Hz), 7.54-7.70 (2H, m), 7.88 (1H, d, J=2 Hz), 7.98 (1H, d, J=6 Hz).

後処理

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with brine and aqueous 2N hydrochloric acid
  5. additionwas added until pH2-3
  6. customThe acid aqueous layer was separated
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-25fe104964ac4f3e8ad5a7850535d88c
出典データセット
uspto-grants-2001_02
特許番号
US06194409B1

関連ノート

読み込み中…