Formic Acid → HCID 86602829, compound

HRID 1444702Notes

Reaction equation

HRID 1444702 reaction equation
C(O[C:4](=[O:6])C)=O.C(O)=O.[C@H:10]1([NH2:20])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1>CCOCC>[C@H:10]1([NH:20][CH:4]=[O:6])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 75269Acetic-formic anhydrideHCID 70580721-Aminotetralin, (R)-

Product 1

HCID 86602829HCID 86602829, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of acetic formic anhydride (0.056 mol) (prepared by stirring acetyl anhydride (7.36 ml, 78.0 mmol) and formic acid (2.94 ml, 78.0 mmol) at 50-60° C. for 2 h then cooling to room temperature) was added (r)-1,2,3,4-tetrahydro-1-naphthylamine (8.20 g, 55.7 mmol) dropwise with stirring at such a rate that the temperature never rose above 40° C. After stirring for 30 min, 300 mL of ether was added, and the solution was stirred at room temperature overnight. The reaction was diluted with ether, washed twice with water, twice with Sat. NaHCO3, with 5% HCl, and finally with water. The organic layer was dried with Na2SO4, filtered, and evaporated to dryness. flash chomatograph (SiO2, hexane/EtOAc=1:1 to pure EtOAc) afforded (R)—N-(1,2,3,4-tetrahydronaphthalen-1-yl)formamide as a white solid.

Workup

  1. stirringAfter stirring for 30 min
  2. stirringthe solution was stirred at room temperature overnight
  3. washwashed twice with water, twice with Sat. NaHCO3, with 5% HCl
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f9bd5271e6974f409b833e757e53fb5b
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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