Formic Acid → Ethyl 7-(Formylamino)chroman-2-carboxylate

HRID 49464Notes

Reaction equation

HRID 49464 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:19]2)=[CH:14][CH:13]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C1COCC1>[CH:1]([NH:11][C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:19]2)=[CH:14][CH:13]=1)=[O:2]

Participants

7

Reactant 5

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 10632774Ethyl 7-Amino-2-chromancarboxylate

Product 1

HCID 20637412Ethyl 7-(Formylamino)chroman-2-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mixed anhydride is prepared by stirring 1.25 equivalents of formic acid and 1 equivalent of acetic anhydride at 60° C. for 2 h. A solution of ethyl 7-amino-2-chromancarboxylate (1.25 g; 5.6 mmol) in THF is treated with triethylamine (0.78 mL; 5.6 mmol) and the previously prepared mixed anhydride (1.6 mL), stirred at ambient temperature for 1 h, poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl ether. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound as a straw colored oil (1.4 g; 100%), identified by NMR spectral analysis.

Workup

  1. customis prepared
  2. customthe previously prepared
  3. extractionextracted with ethyl ether
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e07ca4e470c49a8820efd6faab7f6d4
Source dataset
uspto-grants-2004_03
Patent number
US06706757B2

Reaction notes

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