Pyridine → Methyl 3-(4-(2-acetylhydrazinecarbonyl)phenoxy)-5-(benzyloxy)benzoate

HRID 2098333Notes

Reaction equation

HRID 2098333 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:22]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:24]=1)[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[C:35]([NH:38][NH2:39])(=[O:37])[CH3:36].N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C.Cl>[C:35]([NH:38][NH:39][C:17]([C:16]1[CH:20]=[CH:21][C:13]([O:12][C:11]2[CH:22]=[C:23]([CH:24]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[C:25]([O:27][CH3:28])=[O:26])=[CH:14][CH:15]=1)=[O:19])(=[O:37])[CH3:36]

Participants

8

Reactant 4

HCID 1049PyridineHCID 14039AcetohydrazideHCID 65578Oxalyl chlorideHCID 669721544-[3-(Benzyloxy)-5-(methoxycarbonyl)phenoxy]benzoic acid2×

Product 1

HCID 66972175Methyl 3-(4-(2-acetylhydrazinecarbonyl)phenoxy)-5-(benzyloxy)benzoate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 4-[3-(benzyloxy)-5-(methoxycarbonyl)phenoxy]benzoic acid (Intermediate 11) (34 g, 82.87 mmol, 1 equiv) in dry DCM (50 mL), DMF (1.5 mL, catalytic) was added followed by oxalyl chloride (20.1 g, 158.7 mmol, 2 equiv.) dropwise at 0-5° C. The reaction mixture was stirred at room temperature for 2 h. After 2 h, a mixture of acetic hydrazide (8.8 g, 119 mmol, 1.5 equiv.) and dry pyridine (12.4 mL, 158.7 mmol, 2 equiv.) in dry DCM (50 mL) was added to the above prepared acid chloride at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 15 min. The reaction was monitored by TLC. After completion, the reaction mixture was diluted with dil. HCl and extracted with DCM. The organic layer was washed with water, brine and dried over sodium sulphate and concentrated to afford white solid. (32 g).

Workup

  1. waitAfter 2 h
  2. additionwas added to the
  3. temperatureto warm to room temperature
  4. stirringstirred for 15 min
  5. extractionextracted with DCM
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. customto afford white solid

Sources & evidence

ORD record
ord-58a2becd330e4cebb08eba1b24fcef9b
Source dataset
uspto-grants-2013_05
Patent number
US08450494B2

Reaction notes

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