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

HRID 2367106노트

반응식

HRID 2367106 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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+)

후처리

  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)

출처 및 근거

ORD 기록
ord-1584f0def3014f67a6d7ea26cac19d02
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697737B2

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