Hydrochloric Acid → (3-Bromo-2-methylphenyl)methanamine

HRID 564450Notes

Reaction equation

HRID 564450 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=O.C1COCC1.S(C)C.Cl>CO>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH2:5][NH2:7])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1068Dimethyl SulfideHCID 8028TetrahydrofuranHCID 588288773-Bromo-2-methylbenzamide2×

Product 1

HCID 53414428(3-Bromo-2-methylphenyl)methanamineYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Bromo-2-methylbenzamide (1.4 g) was dissolved with dry THF (15 mL) under nitrogen, then Me2S.BH3 (94%, 1.34 mL) was added slowly. After being stirred at room temperature for 1 h, the mixture was heated to 50° C. overnight. When the 3-bromo-2-methylbenzamide disappeared, methanol was added dropwise until there no more air bubble formed. 10 min later, 10% HCl was added dropwise, stirred for 1 h, and then solvent was removed. The white residue was recrystallized with iPrOH to obtain 1.1 g of the product. Yield: 35%. 1H NMR (400 MHz, DMSO-d6): δ 2.42 (s, 3 H), 4.09 (s, 2 H), 7.20 (t, J=7.8 Hz, 1 H), 7.44 (d, J1=8.0 Hz, 1 H), 7.63 (d, J1=7.6 Hz, 1 H), 8.49 (br, 3 H); 13C NMR (100 MHz, DMSO-d6): δ 18.8, 19.0, 46.1, 125.2, 127.4, 127.5, 129.0, 129.1, 132.1, 132.5, 134.7, 135.9, 136.1, 136.5; HPLC: retention time: 4.696 min; purity: 96.0%.

Workup

  1. additionBH3 (94%, 1.34 mL) was added slowly
  2. temperaturethe mixture was heated to 50° C. overnight
  3. custombubble
  4. customformed
  5. stirringstirred for 1 h
  6. customsolvent was removed
  7. customThe white residue was recrystallized with iPrOH

Sources & evidence

ORD record
ord-e0d30696b10b4fe284f395a6e15bbacf
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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