Hydroxylamine → Methyl 3-[amino(hydroxyimino)methyl]-4-methoxybenzoate

HRID 219853

反応式

HRID 219853 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7])#[N:2].[NH2:15][OH:16]>CCO>[NH2:2][C:1](=[N:15][OH:16])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7]

参加物

4

反応物 2

HCID 787HydroxylamineHCID 2801011Methyl 3-cyano-4-methoxybenzoate

生成物 1

HCID 53410613Methyl 3-[amino(hydroxyimino)methyl]-4-methoxybenzoate収率 98.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of methyl 3-cyano-4-methoxybenzoate (518 mg, 2.71 mmol), hydroxylamine (810 μL, 50% in water, 13.55 mmol) in EtOH (20 mL) was heated for 18 h at 60° C. after which time solvents were removed under vacuum, solid residue was triturated with water filtered and dried under vacuum overnight to give the title compound as an off-white solid (600 mg, quant). 1H NMR (DMSO-d6, 300 MHz) δ 9.48 (s, 1H), 7.97-7.95 (m, 2H), 7.20-7.17 (m, 1H), 5.70 (bs, 2H), 3.87 (s, 3H), 3.82 (s, 3H). LC/MS (Method B): 225.1 (M+H)+.

後処理

  1. customwere removed under vacuum, solid residue
  2. customwas triturated with water
  3. filtrationfiltered
  4. customdried under vacuum overnight

出典と根拠

ORDレコード
ord-a4dfb99051f8486d833d4003466f4670
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

関連ノート

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