Anthranilic Acid → HCID 59679851, compound

HRID 1924083Notes

Reaction equation

HRID 1924083 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[NH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](O)=O>>[N:8]1[C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[O:1][C:12]=1[C:11]1[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=1[NH2:9]

Participants

3

Reactant 2

HCID 227Anthranilic AcidHCID 27624194-Amino-3-hydroxypyridine

Product 1

HCID 59679851HCID 59679851, compoundYield 31.5%

Procedure

3-Hydroxy-4-aminopyridine (2.220 g, 20.0 mmol) and 2-aminobenzoic acid (2.740 g, 20.0 mmol) in polyphosphoric acid (40 mL) were stirred at 140° C. for 6 hrs. The reaction mixture was poured into distilled water and sodium hydroxide was added until pH=8. The precipitate was collected by filtration and further purified by chromatography on silica gel eluted with petroleum ether:ethyl acetate:Et3N (160:40:1) to give 2-(oxazolo[5,4-c]pyridin-2-yl)benzenamine as yellow solid (1.332 g, Yield: 31%). 1H NMR (400 MHz, DMSO-d6) δ: 6.70 (1H, t, J=6.8 Hz), 6.94 (1H, d, J=8.4 Hz), 7.20 (2H, s), 7.33 (1H, t, J=6.8 Hz), 7.80 (1H, d, J=5.6 Hz), 7.95 (1H, d, J=8.4 Hz), 8.53 (1H, d, J=5.6 Hz), 9.05 (1H, s) ; MS(ESI) calcd. for C12H9N3O (m/z): 211, found: 212 [M+1]+.

Workup

  1. additionThe reaction mixture was poured
  2. distillationinto distilled water and sodium hydroxide
  3. additionwas added until pH=8
  4. filtrationThe precipitate was collected by filtration
  5. customfurther purified by chromatography on silica gel
  6. washeluted with petroleum ether:ethyl acetate:Et3N (160:40:1)

Sources & evidence

ORD record
ord-2fa6c52fd41748fbbb7d81cced137aef
Source dataset
uspto-grants-2012_05
Patent number
US08178536B2

Reaction notes

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