Benzyl Bromide → Benzyl 2-(4-amino-3-nitrobenzoyl)benzoate

HRID 2261950ノート

反応式

HRID 2261950 の反応式
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C)C=O>[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([O:12][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:11])=[O:7])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27975222-(4-Amino-3-nitrobenzoyl)benzoic acid

生成物 1

HCID 67044429Benzyl 2-(4-amino-3-nitrobenzoyl)benzoate収率 81%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 2-(4-amino-3-nitrobenzoyl)benzoic acid (50 g, 175 mmol) and potassium carbonate (50 g, 350 mmol) in N,N-dimethylformamide (200 ml), was added benzyl bromide (22.8 ml, 192 mmol). The mixture was stirred at 60° C. for 16 hours, and then partitioned between ethyl acetate (500 mL) and water. The organic portion was washed with 0.2N sodium hydroxide, water, brine, dried over sodium sulfate, filtered and concentrated in-vacuo. The resultant residue was re-crystallized from chloroform and hexanes (1:1) to afford benzyl 2-(4-amino-3-nitrobenzoyl)benzoate (53 g, 81%) as a yellow solid. 1H NMR (400 MHz, d6-DMSO): 8.11 (br s, 1H), 8.06-8.01 (m, 2H), 7.79-7.75 (m, 1H), 7.72-7.65 (m, 2H), 7.46 (d, 1H), 7.28-7.19 (m, 5H), 7.02 (d, 1H), 5.12 (s, 2H); MS (EI) for C21H16N2O5: 377 (MH+)

後処理

  1. custompartitioned between ethyl acetate (500 mL) and water
  2. washThe organic portion was washed with 0.2N sodium hydroxide, water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in-vacuo
  6. customThe resultant residue was re-crystallized from chloroform and hexanes (1:1)

出典と根拠

ORDレコード
ord-94efb2ec7ef741338b6a065932900cbf
出典データセット
uspto-grants-2010_12
特許番号
US07846959B2

反応ノート

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