Dimethylacetamide → HCID 86606906, compound

HRID 2116766Notes

Reaction equation

HRID 2116766 reaction equation
[N:1]1([NH:7][C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11](Br)[CH:10]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C[C:19]([N:21](C)C)=O>[C-]#N.[Zn+2].[C-]#N.[Pd].[Zn].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[N:1]1([NH:7][C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:19]#[N:21])[CH:10]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

7

Reactant 2

HCID 31374DimethylacetamideHCID 86606907HCID 86606907, compound

Product 1

HCID 86606906HCID 86606906, compoundYield 87.4%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23938PalladiumCatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
152.5 °C

Procedure

3-Bromo-4-hydroxybenzoic acid (4-morpholinyl)amide (286 mg, 1 mmol) is suspended in dimethylacetamide (2.9 mL), and thereto are added zinc cyanide (70 mg, 0.6 mmol), 10% Pd/C (53 mg, 0.05 mmol), zinc (36 mg, 0.56 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (28 mg, 0.05 mmol), followed by deaeration under reduced pressure for nitrogen-displacement (×3). The reaction mixture is heated at 150-155° C. and stirred for 1 hour. After cooling, the insoluble materials are removed by filtration and the reaction solution is subjected to HPLC for quantitative analysis. As a result, it is obtained 3-cyano-4-hydroxybenzoic acid (4-morpholinyl)amide (203 mg, 87.4%). Mp: 238-240° C.

Workup

  1. temperatureAfter cooling
  2. customthe insoluble materials are removed by filtration

Sources & evidence

ORD record
ord-256673187ec7484c8befeeef4eccd7ae
Source dataset
uspto-grants-2008_10
Patent number
US07439368B2

Reaction notes

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