Hydrochloric Acid → HCID 3785006, compound

HRID 1426864Notes

Reaction equation

HRID 1426864 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[C:12]1([NH2:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+].Cl>C(O)C>[C:12]1([NH:18][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 852392,6-Dichloro-3-nitropyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 3785006HCID 3785006, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-dichloro-3-nitropyridine (II-1, 193 mg, 1 mmol), phenylamine (III-2, 93 mg, 1 mmol) and sodium bicarbonate (84 mg, 1 mmol) were added to 10 mL anhydrous ethanol, and reacted at room temperature for 24 h. The reaction solution was poured into ice water, and adjusted with diluted HCl to a pH of 5-6, followed by stirring for 30 min, to precipitate a solid. The solid was filtered out, washed with water until neutral, and then dried to obtain compound IV-2 (219 mg, 88), a red solid, mp 95-98° C. 1H NMR (CDCl3) δ 10.28 (1H, b s, NH), 8.47 (1H, d, J=8.4 Hz, ArH-4), 7.66 (2H, d, J=8.0 Hz, ArH-2′, 6′), 7.42 (2H, t, J=8.0 Hz, ArH-3′, 5′), 7.21 (1H, t, J=7.2 Hz, ArH-4′), 6.81 (1H, d, J=8.4 Hz, ArH-5); MS (m/z): 250 (M+).

Workup

  1. customreacted at room temperature for 24 h
  2. customto precipitate a solid
  3. filtrationThe solid was filtered out
  4. washwashed with water until neutral, and
  5. customthen dried
  6. customto obtain compound IV-2 (219 mg, 88)

Sources & evidence

ORD record
ord-89f872d609074dcb8155579bf364bc73
Source dataset
uspto-grants-2015_01
Patent number
US08933106B2

Reaction notes

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