Hydrochloric Acid → HCID 178510577, compound

HRID 1801484Notes

Reaction equation

HRID 1801484 reaction equation
[C:1]([C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[C:5]([Cl:10])[N:4]=1)#[N:2].Cl.[N:12]([O-])=O.[Na+].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O.C(O)C>[C:17]1([N:16]=[N:12][NH:9][C:8]2[C:3]([C:1]#[N:2])=[N:4][C:5]([Cl:10])=[CH:6][CH:7]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 5927503-Amino-6-chloropyridine-2-carbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 178510577HCID 178510577, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-cyano-6-chloro-3-pyridinylamine (0.153 g, 1 mmol) was added into 3 mL of hydrochloric acid (10 mol/L), and then cooled to 0° C. in ice-salt bath. Sodium nitrite (0.072 g) dissolved in water (1.0 mL) was added to the solution dropwise under stirring for 20 min. The diazonium solution was neutralized with 0.093 g of aniline (1.0 mmol) dissolved in anhydrous ethanol to pH 5-6 and stirred for 2 h at 0-5° C. The solution was kept overnight, filtered, and washed with water till colorless to yield the crude product. The crude product was purified on a silica gel column with petroleum ether:ethylacetate (v/v)=20:1 to yield yellow solid product (0.116 g) with a recovery rate of 45.1%.

Workup

  1. additionwas added to the solution dropwise
  2. stirringstirred for 2 h at 0-5° C
  3. waitThe solution was kept overnight
  4. filtrationfiltered
  5. washwashed with water till colorless
  6. customto yield the crude product
  7. customThe crude product was purified on a silica gel column with petroleum ether

Sources & evidence

ORD record
ord-ba34cce18df046a8a0e986db2d14435f
Source dataset
uspto-grants-2013_01
Patent number
US08349835B2

Reaction notes

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