Hydrochloric Acid → HCID 16215363, compound

HRID 912419Notes

Reaction equation

HRID 912419 reaction equation
Cl[C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:14](=[O:17])([O-])[O-].[K+].[K+].Cl>CN(C=O)C.[Cu].C[C@H]1O[C@H]2[C@H](O)[C@@H](O)[C@H](OC3C4C(=CC5OCOC=5C=4)[C@@H](C4C=C(OC)C(O)=C(OC)C=4)[C@@H]4[C@@H]3COC4=O)O[C@@H]2CO1.C1COP(NCCCl)(=O)N(CCCl)C1.[NH2-].[NH2-].Cl[Pt+2]Cl>[NH2:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:6])[C:3]3[C:2]([O:17][C:14]=2[CH:10]=1)=[CH:10][C:9]([N+:11]([O-:13])=[O:12])=[CH:8][CH:7]=3

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 74482-Chloro-4-nitrobenzoic acidHCID 11430Potassium Carbonate

Product 1

HCID 16215363HCID 16215363, compoundYield 162.6%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 56841950ICE protocol 1CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2-chloro-4-nitrobenzoic acid (3 g, 14.88 mmol) in DMF (40 mL) was added 3-3′-acetamidolphenol (2.47 g, 16.38 mmol), potassium carbonate (3.08 g, 16.38 mmol), and copper powder (102 mg, 1.61 mmol). After heating at 130° C. overnight, the reaction mixture was cooled to room temperature and poured to ice—1 N HCl solution (300 mL) slowly. The solution was stirred until the brown solid was formed. The solid was filtered off and washed with cold water to yield a brown solid (3.1 g). A crude solid was dissolved in conc. sulfuric acid (20 mL) and heated at 80° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured to ice (350 mL volume) and stirred for 1 hour. The precipitated solid was filtered off and re-suspended in 2.5% aq. sodium carbonate solution. The solid was filtered and washed with cold water and dried under vacuum. The solid was further recrystallized in pyridine or pyridine/water to yield 1.23 g of S3 (Y═O) (60%, two steps) as a yellowish-brown solid. 1H-NMR (DMSO-d6) δ 8.37 (d, J=2.0, 1H), 8.32 (d, J=8.4, 1H), 8.15 (dd, J=2.0, 8.4, 1H), 7.88 (d, J=8.8, 1H), 6.75 (bs, 2H), 6.72 (dd, J=2.0, 8.8, 1H), 6.56 (d, J=2.0, 1H). ESI-MS m/z (H+H) calc'd: 257.2. found 257.1.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customwas formed
  3. filtrationThe solid was filtered off
  4. washwashed with cold water

Sources & evidence

ORD record
ord-90935f5eb89e40ada059e0292b359ac0
Source dataset
uspto-grants-2011_09
Patent number
US08026110B2

Reaction notes

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