Sodium Carbonate → HCID 86636829, compound

HRID 548973Notes

Reaction equation

HRID 548973 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]2[C:11]3[C:12](O)=[N:13][CH:14]=[CH:15][C:16]=3[O:17][C:9]=2[C:8]([O:19][CH3:20])=[CH:7][CH:6]=1)=[O:4].P(Cl)(Cl)([Cl:23])=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][O:2][C:3]([C:5]1[C:10]2[C:11]3[C:12]([Cl:23])=[N:13][CH:14]=[CH:15][C:16]=3[O:17][C:9]=2[C:8]([O:19][CH3:20])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178498264HCID 178498264, compound

Product 1

HCID 86636829HCID 86636829, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of Methyl-1-hydroxy-6-Methoxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylate (from step 10) (1.1 g) and phosphorous oxychloride (25 mL) was refluxed for 15-16 hours. Excess of phosphorous oxychloride was removed under vacuo. The residue obtained was diluted with water (10.0 mL) and made alkaline with solid sodium carbonate. The solid separated was filtered, washed with water and dried to get crude intermediate-12 (1.0 g) as brown solid. Purification by silica gel column using chloroform: ethyl acetate (9:1) as an eluent gave pure intermediate-12 (350 mg) as light yellow solid

Workup

  1. customExcess of phosphorous oxychloride was removed under vacuo
  2. customThe residue obtained
  3. customThe solid separated
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried
  7. customto get crude intermediate-12 (1.0 g) as brown solid
  8. customPurification by silica gel column
  9. customgave pure intermediate-12 (350 mg) as light yellow solid

Sources & evidence

ORD record
ord-36aa43e35dc547b996df907c47b8fb0e
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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