Hydrochloric Acid → HCID 43560608, compound

HRID 241322Notes

Reaction equation

HRID 241322 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([O:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH:5]=1.Cl>CO.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH:5]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 594437631239278-72-8

Product 1

HCID 43560608HCID 43560608, compoundYield 95.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Cyclopropylmethoxy-4-nitro-benzoic acid methyl ester (12.7 g) was dissolved in MeOH (100 ml) and EtOAc (100 ml); 10% Pd/C (1.0 g, suspended in 20 ml of water) was added, and the mixture is hydrogenated in a Parr apparatus (H2: 20 psi) for 5 hours. 37% HCl was added (10 ml), and hydrogenation was continued for additional 2 hours to obtain complete conversion. The catalyst was filtered over a celite pad, the mixture was diluted with EtOAc (200 ml) and washed with an aqueous saturated solution of NaHCO3 (2×100 ml). The organic layer was dried over Na2SO4 and the solvent was removed by evaporation to yield 10.7 g of the desired intermediate.

Workup

  1. waitwas continued for additional 2 hours
  2. customto obtain complete conversion
  3. filtrationThe catalyst was filtered over a celite pad
  4. additionthe mixture was diluted with EtOAc (200 ml)
  5. washwashed with an aqueous saturated solution of NaHCO3 (2×100 ml)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-1129a0cfb1e44aaabcb324a92a043a64
Source dataset
uspto-grants-2014_02
Patent number
US08648204B2

Reaction notes

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