Hydrochloric Acid → 2-Amino-5-bromo-N-(2-methoxy-benzyl)-benzamide

HRID 1243661

반응식

HRID 1243661 반응식
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].C[Al](C)C.C[O:16][C:17](=O)[C:18]1[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:19]=1[NH2:25].Cl>C1(C)C=CC=CC=1>[NH2:25][C:19]1[CH:20]=[CH:21][C:22]([Br:24])=[CH:23][C:18]=1[C:17]([NH:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[O:2][CH3:1])=[O:16]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 812922-MethoxybenzylamineHCID 736224Methyl 2-amino-5-bromobenzoateHCID 16682925Trimethylaluminum

생성물 1

HCID 219302782-Amino-5-bromo-N-(2-methoxy-benzyl)-benzamide

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Under a nitrogen atmosphere, 2-methoxy benzylamine (10 g, 73 mmol) was suspended in anhydrous toluene (30 ml). This suspension was cooled down in ice bath and (2 M) trimethyl aluminum solution in hexanes (36 ml, 72 mmol) was added slowly. The reaction mixture was stirred at room temperature for 1 hour after the completion of the addition. The resulting solution was then cooled in an ice bath and methyl-2-amino-5-bromobenzoate was added in small portions. The reaction was allowed to stir at room temperature overnight. This solution was poured into a pre-cooled solution 2N HCl (300 ml). The solid obtained was collected by filtration and triturated in methanol (50 ml). The solid was collected and dried under high vacuum oven at 65° C. overnight. Pure product was recovered (16 g). 1H NMR (DMSO) δ=3.8 (s, 3H), 4.35 (sd, 2H), 6.5 (2H), 6.6 (1H), 6.85 (1H), 6.9 (1H), 7.1–7.25 (3H), 7.7 (1H), 8.7 (br, 1H).

후처리

  1. temperatureThis suspension was cooled down in ice bath
  2. additionafter the completion of the addition
  3. temperatureThe resulting solution was then cooled in an ice bath
  4. stirringto stir at room temperature overnight
  5. customThe solid obtained
  6. filtrationwas collected by filtration
  7. customtriturated in methanol (50 ml)
  8. customThe solid was collected
  9. customdried under high vacuum oven at 65° C. overnight
  10. customPure product was recovered (16 g)

출처 및 근거

ORD 기록
ord-45fb4ab79464446b9138a1a96c3e3d2f
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119120B2

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