Indoline → HCID 23287691, compound

HRID 367168Notes

Reaction equation

HRID 367168 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[S-:15][C:16]#[N:17].[NH4+].[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20]1>CC(C)=O.CN(C=O)C>[N:19]1([C:16]2[S:15][C:2]3[N:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4](=[O:6])[N:17]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 10328IndolineHCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 23287691HCID 23287691, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 57 was followed except that 1.728 mg (10.97 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 913 mg of ammonium thiocyanate, 15 ml of acetone, 1.31 g of indoline and 10 ml of acetone were used. As a result, 2.45 g of 2-(indolin-1-yl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one was obtained.

Workup

  1. customThe reaction procedure of Example 57

Sources & evidence

ORD record
ord-782d01e554964f3eba8a94e0c4f0bc53
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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