Hydrochloric Acid → Methyl 4-(Acetylamino)-3-Aminobenzoate, Hydrochloride

HRID 2400188Notes

Reaction equation

HRID 2400188 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-])=O)(=[O:3])[CH3:2].[ClH:18].O.NN>C(O)C.[Pd]>[ClH:18].[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[NH2:15])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 236856Methyl 4-(acetylamino)-3-nitrobenzoate

Product 1

HCID 131719127Methyl 4-(Acetylamino)-3-Aminobenzoate, HydrochlorideYield 78.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a suspension of 15 (0.870 g, 3.65 mmol) in ethanol (30 mL) was added Pd-C (0.87 g) and 5% HCl (0.85 mL). Hydrazine hydrate (55% hydrazine, 0.85 mL, 0.47 g, 15 mmol) dissolved in ethanol (SmL) was then added dropwise to the above mixture. The reaction mixture was stirred at room temperature for 1/2 hour and the Pd-C was filtered. The filtrate was concentrated under vacuum to give 16 (0.500 g, 78.7% yield) as a white solid: mp 187°-190° C.

Workup

  1. additionwas then added dropwise to the above mixture
  2. filtrationthe Pd-C was filtered
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-2c9398ca95444f8fac30bdb09fc2053d
Source dataset
uspto-grants-1995_09
Patent number
US05453533

Reaction notes

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