(4-Nitrophenyl)acetic acid → 7,8-Dimethoxy-6-nitro-3-(4-nitro-phenyl)-chromen-2-one

HRID 965776Notes

Reaction equation

HRID 965776 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[C:7]([N+:14]([O-:16])=[O:15])=[CH:6][C:3]=1[CH:4]=O.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](O)=[O:28])=[CH:22][CH:21]=1)([O-:19])=[O:18].C(N(CC)CC)C.P(Cl)(Cl)(OC1C=CC=CC=1)=O>ClCCCl.C(Cl)Cl>[CH3:13][O:12][C:8]1[C:9]([O:10][CH3:11])=[C:2]2[C:3]([CH:4]=[C:26]([C:23]3[CH:22]=[CH:21][C:20]([N+:17]([O-:19])=[O:18])=[CH:25][CH:24]=3)[C:27](=[O:28])[O:1]2)=[CH:6][C:7]=1[N+:14]([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 8471TriethylamineHCID 13038Phosphorodichloridic acid, phenyl esterHCID 223134323,4-Dimethoxy-2-hydroxy-5-nitrobenzaldehyde2×

Product 1

HCID 223134527,8-Dimethoxy-6-nitro-3-(4-nitro-phenyl)-chromen-2-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-hydroxy-3,4-dimethoxy-5-nitro-benzaldehyde obtained from Preparation Example (1a) (0.46 g), 4-nitrophenyl acetic acid (0.39 g) and triethylamine (0.84 ml) in 1,2-dichloroethane (30 ml) was treated with phenyl dichlorophosphate (0.44 ml) at 0° C. The mixture was refluxed for 5 hours and cooled. The cool reaction mixture was diluted with methylene chloride, washed successively with 2.5 M NaOH, 2 M HCl and water, dried and evaporated. The product was finally triturated with pethroleum ether and filtered. Yield: 0.52 g, melting point 219-223° C.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. temperaturecooled
  3. customThe cool reaction mixture
  4. washwashed successively with 2.5 M NaOH, 2 M HCl and water
  5. customdried
  6. customevaporated
  7. customThe product was finally triturated with pethroleum ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-762ea51a00434bb4a1b3408027f96354
Source dataset
uspto-grants-2005_10
Patent number
US06951870B2

Reaction notes

Loading…