Dimethylformamide → HCID 67079412, compound

HRID 453392Notes

Reaction equation

HRID 453392 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:13]=[C:12](Br)[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[NH2:15].[CH3:17][N:18](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:13]=[C:12]([C:17]#[N:18])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[NH2:15]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 23436066Dimethyl 2-amino-5-bromobenzene-1,4-dicarboxylate

Product 1

HCID 67079412HCID 67079412, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

2-Amino-5-bromo-terephthalic acid dimethyl ester (15.0 g, 52.1 mmol), zinc (II) cyanide (6.11 g, 52.1 mmol) and tetrakis(triphenylphosphine)palladium (0) (3.0 g, 2.6 mmol) were suspended in DMF (50 ml) and the resultant reaction mixture degassed was purged with argon. The reaction mixture was heated at 120° C. for 30 minutes then concentrated in vacuo. The resultant residue was triturated with hot water (100 ml) and the product collected by filtration to yield the title compound as a dark grey solid (12.0 g, 98%). 1H NMR (d6-DMSO, 400 MHz) 8.11 (1H, s), 7.62 (2H, br s), 7.52 (1H, s), 3.89 (3H, s), 3.85 (3H, s).

Workup

  1. customthe resultant reaction mixture
  2. customdegassed
  3. customwas purged with argon
  4. concentrationthen concentrated in vacuo
  5. customThe resultant residue was triturated with hot water (100 ml)
  6. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-a2de2e361ac14f04a0543df2b80bea9b
Source dataset
uspto-grants-2013_07
Patent number
US08492427B2

Reaction notes

Loading…