Acetic Acid → 5,6-Diaminonicotinic acid

HRID 397492Notes

Reaction equation

HRID 397492 reaction equation
Cl[Sn]Cl.[N+:4]([C:7]1[C:8]([NH2:16])=[N:9][CH:10]=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13])([O-])=O.N.C(O)(=O)C>Cl>[NH2:4][C:7]1[C:8]([NH2:16])=[N:9][CH:10]=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 24479Stannous ChlorideHCID 2718816-Amino-5-nitronicotinic acid

Product 1

HCID 224762985,6-Diaminonicotinic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

See Markwald, W. Chem. Ber. 1984, 27, 1317. To a stirred solution of SnCl2 (4.16 g, 22.0 mmol) in concentrated HCl (11 mL) at 0° C. was added in portions 5-nitro-6-aminonicotinic acid (1.01 g, 5.5 mmol). The resulting orange mixture was then heated to 100° C. under argon for 75 min. The mixture was then cooled to RT and was then placed in an ice bath and neutralized with concentrated aqueous ammonia (to pH 6-7), resulting in a thick cream-colored mixture. The mixture was then acidified to pH 4 with acetic acid and the precipitate collected by filtration, washed with H2O and dried under vacuum overnight to afford the title compound: 1H NMR (300 MHz, DMSO-d6): δ7.98 (d, J=2.1 Hz, 1H), 7.21 (d, J=2.1 Hz, 1H), 6.24 (br s, 2H), 5.00 (br s, 2H).

Workup

  1. temperatureThe mixture was then cooled to RT
  2. customresulting in a thick cream-colored mixture
  3. filtrationthe precipitate collected by filtration
  4. washwashed with H2O
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-866e44f325744d56aa99a23a87f2be19
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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