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

HRID 1243661

Reaction equation

HRID 1243661 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-45fb4ab79464446b9138a1a96c3e3d2f
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Linked notes

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