Hydrochloric Acid → HCID 16774264, compound

HRID 2086826Notes

Reaction equation

HRID 2086826 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.C(=O)(O)[O-].[Na+]>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 7780003N-(3-nitrophenyl)-2-naphthalenecarboxamide

Product 1

HCID 16774264HCID 16774264, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-(3-nitrophenyl)-2-naphthalenecarboxamide (2.94 g), iron powder (3.0 g) and hydrochloric acid (35%, 9 ml) in ethanol (30 ml) was stirred at 80° C. for 2 hours. 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 N-(3-aminophenyl)-2-naphthalenecarboxamide (2.17 g).

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-2964a4a6f6494314851f93d49e939df8
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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