Hydrochloric Acid → Methanone, (2-aminophenyl)[4-(phenylmethoxy)phenyl]-

HRID 344834ノート

反応式

HRID 344834 の反応式
CON(C)[C:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7].[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Li]CCCC.Cl>O1CCCC1>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[NH2:7])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 110522422-amino-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

生成物 1

HCID 10935571Methanone, (2-aminophenyl)[4-(phenylmethoxy)phenyl]-

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of N-methoxy-N-methyl anthranilic acid amide prepared as in Example 1(A)(2.00 g, 11.1 mmol) and 4-benzyloxy-bromobenzene (2.92 g, 11.1 mmol) in anhydrous tetrahydrofuran (65 ml) at -78° C. under nitrogen is added, with vigorous stirring, n-BuLi in hexanes (13.8 ml, 1.6M, 22.2 mmol) at 0.60 ml/min. After 20 min, aqueous hydrochloric acid is added (1N, 20 ml), the mixture extracted with ethyl acetate (150 ml), ethyl acetate washed with water, brine, dried over magnesium sulfate, and concentrated. Recrystallization from hexanes gave 4'-benzyloxy-2-aminobenzophenone as yellow crystals; yield: 2.35 g, (70%); m.p. 99°-101° C.

後処理

  1. customat -78° C.
  2. extractionthe mixture extracted with ethyl acetate (150 ml), ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customRecrystallization from hexanes

出典と根拠

ORDレコード
ord-117daf84d97946babe1347d2abf4bc03
出典データセット
uspto-grants-1991_10
特許番号
US05053543

反応ノート

読み込み中…