Formic Acid → HCID 20094744, compound

HRID 274068Notes

Reaction equation

HRID 274068 reaction equation
[CH2:1]([N:8]([CH:11]1[CH2:17][CH2:16][CH2:15][C:14]2[CH:18]=[CH:19][C:20]([NH2:22])=[CH:21][C:13]=2[CH2:12]1)[CH:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:23](O)=[O:24]>>[CH2:1]([N:8]([CH:11]1[CH2:17][CH2:16][CH2:15][C:14]2[CH:18]=[CH:19][C:20]([NH:22][CH:23]=[O:24])=[CH:21][C:13]=2[CH2:12]1)[CH:9]=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 20094825HCID 20094825, compound

Product 1

HCID 20094744HCID 20094744, compound

Procedure

A solution of N-benzyl-N-formyl-(3-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (0.80 g) in formic acid (16 ml) was refluxed for 2 hours. After cooling, the solution was evaporated in vacuo. The residue was dissolved in ethyl acetate and the solution was washed successively with 1N sodium hydroxide solution, 1N hydrochloric acid, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (20:1) as an eluent to give N-benzyl-N-formyl-(3-formylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (0.84 g).

Workup

  1. temperatureAfter cooling
  2. customthe solution was evaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed successively with 1N sodium hydroxide solution, 1N hydrochloric acid, and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (20:1) as an eluent

Sources & evidence

ORD record
ord-cdd89780e0374cf0bd348a2558e2bd03
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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