2-Amino-6-methylpyridine → HCID 18457531, compound

HRID 2117787Notes

Reaction equation

HRID 2117787 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[Br:9]Br>C(O)(=O)C>[BrH:9].[Br:9][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][C:4]=1[CH3:8]

Participants

4

Reactant 2

HCID 157652-Amino-6-methylpyridineHCID 24408Bromine

Product 1

HCID 18457531HCID 18457531, compoundYield 147.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Conditions

Temperature
35 °C

Procedure

2-Amino-6-picoline (39.8 kg, 99.6 wgt % purity, 367 mol, 1.00 eq) was charged into acetic acid (65.0 kg) while the temperature rose to 60° C. Additional acetic acid (17 kg) was charged to wash in the last of the picoline and the mixture was heated to 35° C. until dissolution occurred. After cooling to 18° C., bromine (56.2 kg, 352 mol, 0.96 eq) was charged at 18±3° C. over 2 hours. More acetic acid (2.0 kg) was charged to wash in the last of the bromine. The mixture was held at this temperature range for 1 hour and then cooled to 11-15° C. It was held in this range for 0.5 hours. The solids were recovered by filtration on polypropylene and washed with isopropanol (63.0 kg) to produce 69.6 kg of moist 5-bromo-2-amino-6-picoline hydrobromide (76 wgt % of product as hydrobromide). This corresponds to a 54% yield. Part of this product was dried for the purposes of recording the 13C NMR spectrum: 13C NMR (400 MHz, DMSO-d6) δ 154.1, 146.9, 112.4, 105.2, 20.1.

Workup

  1. customrose to 60° C
  2. washto wash in the last of the picoline
  3. temperatureAfter cooling to 18° C.
  4. washto wash in the last of the bromine
  5. temperaturecooled to 11-15° C
  6. waitIt was held in this range for 0.5 hours
  7. filtrationThe solids were recovered by filtration on polypropylene
  8. washwashed with isopropanol (63.0 kg)

Sources & evidence

ORD record
ord-1547b73faebf47c88799f8cd45a91b4c
Source dataset
uspto-grants-2008_10
Patent number
US07442792B2

Reaction notes

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