Hydroxylamine → 6-[amino(hydroxyimino)methyl]-1H-indole-2-carboxylic acid

HRID 400770ノート

反応式

HRID 400770 の反応式
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([OH:14])=[O:13])[NH:9]2)=[CH:5][CH:4]=1)#[N:2].[NH2:15][OH:16]>CCO>[NH2:2][C:1](=[N:15][OH:16])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([OH:14])=[O:13])[NH:9]2)=[CH:5][CH:4]=1

参加物

4

反応物 2

HCID 787HydroxylamineHCID 105836876-cyano-1H-indole-2-carboxylic Acid

生成物 1

HCID 767874196-[amino(hydroxyimino)methyl]-1H-indole-2-carboxylic acid収率 104.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

A solution of 6-cyano-1H-indole-2-carboxylic acid (prepared according to J. Org. Chem. 1953, 18, 345-357, 1 g; 5.37 mmol; 1 eq.), hydroxylamine (50% in water; 1.77 mL; 26.86 mmol; 5 eq.) in EtOH (10 mL) was stirred at RT for 14 hours after which it was further heated at 60° C. for 28 hours. Solvents were removed under vacuum to give the title compound as a white powder (1.227 g; quantitative yield). 1H NMR (DMSO-d6) δ 11.75 (s, 1H), 7.72 (s, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.37 (dd, J=1.2, 8.5 Hz, 1H), 7.00 (d, J=1.2 Hz, 1H), 5.76 (bs, 2H), 3.44 (q, J=7.1 Hz, 2H), 1.05 (t, J=7.1 Hz, 3H).

後処理

  1. customSolvents were removed under vacuum

出典と根拠

ORDレコード
ord-7b2bb573718f4de0b45f300c72392727
出典データセット
uspto-grants-2014_06
特許番号
US08741923B2

反応ノート

読み込み中…