Stannous Chloride → HCID 21710146, compound

HRID 650911Notes

Reaction equation

HRID 650911 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]2[C:3]=1[CH2:4][N:5]([CH:13]([CH3:15])[CH3:14])[C:6]2=[O:12].[N:16]([O-])=O.[Na+].[Sn](Cl)Cl>Cl.O>[ClH:11].[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([NH:1][NH2:16])=[C:3]2[C:7]=1[C:6](=[O:12])[N:5]([CH:13]([CH3:15])[CH3:14])[CH2:4]2

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 21710150HCID 21710150, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21710146HCID 21710146, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A stirred solution of 4.0 grams (0.018 mole) of 4-amino-7-chloro-2-(1-methylethyl)isoindolin-1-one in 40 mL of concentrated hydrochloric acid was cooled in an ice-water bath, and a solution of 1.2 grams (0.018 mole) of sodium nitrite in 20 mL of water was added dropwise while maintaining the reaction mixture temperature under 5° C. Upon completion of addition, the reaction mixture was stirred for about 45 minutes, then a solution of 8.8 grams (0.039 mole) of tin(II) chloride in 20 mL of concentrated hydrochloric acid was added dropwise while still maintaining the reaction mixture temperature under 5° C. After this time the reaction mixture was stirred for about one hour at 5° C., then it was filtered to collect, after drying, 4.6 grams of subject compound, mp 186° C., dec. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperaturewhile still maintaining the reaction mixture temperature under 5° C
  3. stirringAfter this time the reaction mixture was stirred for about one hour at 5° C.
  4. filtrationit was filtered
  5. customto collect
  6. customafter drying

Sources & evidence

ORD record
ord-4320506219ca4011bf0039eb0c635776
Source dataset
uspto-grants-2001_08
Patent number
US06277847B1

Reaction notes

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