Hydrochloric Acid → HCID 43330295, compound

HRID 1426863Notes

Reaction equation

HRID 1426863 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]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)#[N:13].CC(C)([O-])C.[K+].Cl>CN(C)C=O>[Cl:11][C:4]1[N:3]=[C:2]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 133964-AminobenzonitrileHCID 852392,6-Dichloro-3-nitropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 43330295HCID 43330295, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Dichloro-3-nitropyridine (II-1, 193 mg, 1 mmol) and p-cyanophenylamine (III-1, 236 mg, 2 mmol) were dissolved in N,N-dimethylformamide (DMF, 3 mL). While cooling in ice bath, potassium t-butoxide (224 mg, 2 mmol) was added in batch, followed by reacting at room temperature for 2 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, dried, and separated via a silica gel column (dichloromethane as eluant), to obtain compound IV-1 (186 mg, 68%), a pale yellow solid, mp 175-178° C. 1H NMR (CDCl3) δ 10.47 (1H, br s, NH), 8.53 (1H, d, J=8.4 Hz, ArH-4), 7.86 (2H, d, J=8.8 Hz, ArH-2′, 6′), 7.70 (2H, d, J=8.8 Hz, ArH-3′, 5′), 6.96 (1H, d, J=8.4 Hz, ArH-5); MS (m/z): 275 (M+).

Workup

  1. temperatureWhile cooling in ice bath
  2. customto precipitate a solid
  3. filtrationThe solid was filtered out
  4. washwashed with water until neutral,
  5. customdried
  6. customseparated via a silica gel column (dichloromethane as eluant)
  7. customto obtain compound IV-1 (186 mg, 68%)

Sources & evidence

ORD record
ord-82cbd1cb083a4d0a90f4622ad1a2bbe1
Source dataset
uspto-grants-2015_01
Patent number
US08933106B2

Reaction notes

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