Methylamine → HCID 47315722, compound

HRID 533294Notes

Reaction equation

HRID 533294 reaction equation
CO[C:3](=[O:15])[CH:4]([NH:6][C:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:8])[CH3:5].[CH3:16][NH2:17]>C(O)C>[CH3:16][NH:17][C:3]([CH:4]([NH:6][C:7](=[O:8])[C:9]1[CH:14]=[CH:13][CH:12]=[N:11][CH:10]=1)[CH3:5])=[O:15]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 19166803HCID 19166803, compound

Product 1

HCID 47315722HCID 47315722, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-[(pyridine-3-carbonyl)-amino]-propionic acid methyl ester (10.4 g, 50 mmol) in ethanol (50 mL) was added methylamine (24 g, 33 wt % solution in ethanol, 250 mmol). The reaction mixture was heated at 55° C. for 45 min. The solvents were removed in vacuo and the residue was recrystallized from hot ethyl acetate and hexanes. The yellow crystals thus obtained were washed with cold ethyl acetate and dried to give the desired product (5.2 g, 50%): 1H NMR (300 MHz, DMSO-d6) δ 9.05 (br s, 1H), 8.77-8.70 (m, 2H), 8.24 (m, 2H), 7.89 (br s, 1H), 7.50 (m, 1H), 2.59 (d, J=4.7 Hz, 3H), 1.33 (d, J=7.4 Hz, 3H); ESIMS m/z 208.1 (M+1), m/z 206.1 (M−1).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was recrystallized from hot ethyl acetate and hexanes
  3. customThe yellow crystals thus obtained
  4. washwere washed with cold ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-96e9882a2eaa44ceb0e7fe4aace4942d
Source dataset
uspto-grants-2014_10
Patent number
US08853246B2

Reaction notes

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