Isonicotinic Acid → HCID 178473973, compound

HRID 858299Notes

Reaction equation

HRID 858299 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[CH2:6][C:5]1=[O:14])(=[O:3])[CH3:2].[N:15]1[CH:20]=[CH:19][C:18]([C:21](O)=[O:22])=[CH:17][CH:16]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C(O)(=O)C.O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[C:6](=[C:21]([OH:22])[C:18]2[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=2)[C:5]1=[O:14])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 5922Isonicotinic AcidHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 116441611-Acetyl-6-chloro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 178473973HCID 178473973, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6.3 g of 1-acetyl-6-chloro-2-indolinone, 4.06 g pyridine-4-carboxylic acid, 10.6 g TBTU and 21 ml triethylamine are stirred in 60 ml of DMF for 15 hours at ambient temperature. The mixture is combined with water, then adjusted to pH 5 by the addition of 10% acetic acid. The precipitate is suction filtered, washed with water and taken up in ethyl acetate. The solution obtained is dried with sodium sulphate and evaporated almost to dryness. The precipitate obtained is suction filtered and dried at 100° C.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customThe solution obtained
  4. dry with materialis dried with sodium sulphate
  5. customevaporated almost to dryness
  6. customThe precipitate obtained
  7. filtrationfiltered
  8. customdried at 100° C.

Sources & evidence

ORD record
ord-5a3491756720439c9500648334c12073
Source dataset
uspto-grants-2006_12
Patent number
US07148249B2

Reaction notes

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