Water → 3-Amino-6-bromo-N-methylpicolinamide

HRID 2279727Notes

Reaction equation

HRID 2279727 reaction equation
[CH3:1][NH2:2].O.C(O[C:7]([C:9]1[C:14]([NH2:15])=[CH:13][CH:12]=[C:11]([Br:16])[N:10]=1)=[O:8])C>CO>[NH2:15][C:14]1[C:9]([C:7]([NH:2][CH3:1])=[O:8])=[N:10][C:11]([Br:16])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 25137688Ethyl 3-amino-6-bromopicolinate2×

Product 1

HCID 866976863-Amino-6-bromo-N-methylpicolinamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A 10M solution of Methylamine in H2O (30.0 mL, 386 mmol) was added to a stainless steel reactor containing 3-amino-6-bromopyridine-2-carboxylic acid ethyl ester (Compound 6E, 7.614 g, 31.07 mmol) in MeOH (20.0 mL). The reactor was sealed and heated to 100° C. for 16 hours. The cooled reaction mixture was transferred to a round bottom flask and concentrated in vacuo forming a yellow precipitate which was collected by filtration. Further precipitate formed in the filtrate which was also collected. The combined precipitates were dried in vacuo to afford the title compound as 6.18 g of a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.80 (br. s., 1H), 7.27 (d, J=8.6 Hz, 1H), 6.91 (d, J=8.6 Hz, 1H), 6.02 (br. s., 2H), 2.97 (d, J=5.1 Hz, 3H).

Workup

  1. customThe reactor was sealed
  2. customThe cooled reaction mixture
  3. customwas transferred to a round bottom flask
  4. concentrationconcentrated in vacuo
  5. customforming a yellow precipitate which
  6. filtrationwas collected by filtration
  7. customFurther precipitate formed in the filtrate which
  8. customwas also collected
  9. customThe combined precipitates
  10. customwere dried in vacuo

Sources & evidence

ORD record
ord-e3afbf3742124a1d82874b908926c500
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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