Hydrochloric Acid → HCID 22724458, compound

HRID 2231004Notes

Reaction equation

HRID 2231004 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[CH:15]=[C:16]([NH:20][C:21]2[C:26]([N+:27]([O-])=O)=[CH:25][CH:24]=[CH:23][N:22]=2)[CH:17]=[CH:18][CH:19]=1)=[O:12].Cl.C(=O)(O)[O-].[Na+]>C(O)C.[Fe]>[NH2:27][C:26]1[C:21]([NH:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([NH:13][C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)=[O:12])[CH:15]=2)=[N:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22724164HCID 22724164, compound

Product 1

HCID 22724458HCID 22724458, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[3-(2-naphthoylamino)phenylamino]-3-nitropyridine (948 mg), iron powder (0.55 g) and hydrochloric acid (35%, 2 ml) in ethanol (8 ml) was stirred at 80° C. for 30 minutes. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 3-amino-2-[3-(2-naphthoylamino)phenylamino]pyridine (682 mg).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-cb6080cb1db54ac4960895b263d41c4b
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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