Sodium Acetate → HCID 86654801, compound

HRID 521530Notes

Reaction equation

HRID 521530 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O)=[O:2].Cl.[CH3:15][O:16][C:17]([C:19]1([NH2:28])[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20]1)=[O:18].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:15][O:16][C:17]([C:19]1([NH:28][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([CH:1]=[O:2])[CH:4]=2)[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20]1)=[O:18]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 190399693-Formyl-4-methoxybenzoic acidHCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochloride

Product 1

HCID 86654801HCID 86654801, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Formyl-4-methoxy-benzoic acid (F. D. Chattaway and F. Calvet, J. Chem. Soc. (1928), 2913-2918) (1.017 g, 5.65 mmol) was reacted with 2-amino-indane-2-carboxylic acid methyl ester hydrochloride in analogy to step 4 of example 3. The obtained product (1.895 g) was dissolved in acetic acid (20 ml), sodium acetate (0.57 g, 6.96 mmol) was added and the mixture was stirred under reflux for 24 h. The volatiles were evaporated in vacuo, the residue partitioned between a saturated sodium hydrogencarbonate solution and EA, and the aqueous phase extracted with EA. The combined organic phases were dried over sodium sulfate and evaporated to dryness to yield 1.52 g of the title compound.

Workup

  1. temperatureunder reflux for 24 h
  2. customThe volatiles were evaporated in vacuo
  3. customthe residue partitioned between a saturated sodium hydrogencarbonate solution and EA
  4. extractionthe aqueous phase extracted with EA
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-815455bc569a4d7ca80ecaaa5701bee1
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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