Water → HCID 57428265, compound

HRID 2264135Notes

Reaction equation

HRID 2264135 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-])=O)[CH:10]=1)[C:5]([OH:7])=[O:6].O>CO.Cl.[Pd]>[ClH:1].[NH2:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 2

HCID 962WaterHCID 2214843-Chloro-5-nitrobenzoic acid

Product 1

HCID 57428265HCID 57428265, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 3-chloro-5-nitrobenzoic acid (10.0 g) and 10% Pd/C (0.3 g) in MeOH (100 mL) and 6N HCl (30 mL) was shaken under 30 psi H2 in a Parr apparatus for 30 min, then filtered through Celite and evaporated. The residue was crystallized from 6N HCl to yield the product. More highly purified material was obtained by a second crystallization from water. 1H-NMR (d4-CD3OD): δ 7.24 (1H, dd, J=1.4, 2.0 Hz), 7.20 (1H, dd, J=1.6, 2.0 Hz), 6.87 (1H, t, J=2.0 Hz). 13C-NMR (d4-CD3OD): δ 167.6, 149.5, 134.3, 132.7, 117.8, 117.4, 113.9.

Workup

  1. filtrationfiltered through Celite
  2. customevaporated
  3. customThe residue was crystallized from 6N HCl
  4. customto yield the product

Sources & evidence

ORD record
ord-74318433dddd445f8ae0a60742124a7d
Source dataset
uspto-grants-2010_12
Patent number
US07855192B2

Reaction notes

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