Formic Acid → HCID 14181210, compound

HRID 728080Notes

Reaction equation

HRID 728080 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[CH2:11]([N:14]([CH2:27][CH2:28][CH3:29])[CH:15]1[CH2:24][CH2:23][C:22]2[C:17](=[C:18]([CH2:25][NH2:26])[CH:19]=[CH:20][CH:21]=2)[CH2:16]1)[CH2:12][CH3:13].[OH-].[Na+]>CCOCC.O>[CH2:27]([N:14]([CH2:11][CH2:12][CH3:13])[CH:15]1[CH2:24][CH2:23][C:22]2[C:17](=[C:18]([CH2:25][NH:26][CH:5]=[O:7])[CH:19]=[CH:20][CH:21]=2)[CH2:16]1)[CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 14181206HCID 14181206, compound

Product 1

HCID 14181210HCID 14181210, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

2.04 ml (21.5 mmol) of acetic anhydride and 0.86 ml (22.8 mmol) of formic acid were stirred for 2 h at +60° C. under nitrogen. After cooling to room temperature, 2.6 g (10 mmol) of 2-dipropylamino-8-aminomethyl-1,2,3,4-tetrahydronaphthalene were added dropwise at a maximum of +25° C. After 15 minutes post-reaction, 5 ml of ether were added. The batch was subsequently stirred for a further 18 h at room temperature and then diluted with 20 ml of ether and 20 ml of water. The aqueous phase was adjusted to pH 9 using 1N sodium hydroxide solution and extracted with ether. The organic phase now obtained was washed with water and dried over sodium sulphate, and the solvent was removed by distillation. The residue was recrystallized from petroleum ether 60-80.

Workup

  1. additionwere added
  2. extractionextracted with ether
  3. customThe organic phase now obtained
  4. washwas washed with water
  5. dry with materialdried over sodium sulphate
  6. customthe solvent was removed by distillation
  7. customThe residue was recrystallized from petroleum ether 60-80

Sources & evidence

ORD record
ord-4409c7e525a3433b98702c781b889713
Source dataset
uspto-grants-1991_09
Patent number
US05047422

Reaction notes

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