Triethylamine → 2-Tetralone-6-carboxamide

HRID 2289666Notes

Reaction equation

HRID 2289666 reaction equation
[C:1]1(=[O:14])[C:10]2[C:5](=CC(C(O)=O)=C[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.O[N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=O.C1(N=C=NC2CCCCC2)CCCCC1.[Cl-].[NH4+].C(N(CC)CC)C>C(Cl)Cl>[CH2:2]1[C:3]2[C:17](=[CH:18][C:19]([C:20]([NH2:16])=[O:21])=[CH:5][CH:4]=2)[CH2:9][CH2:10][C:1]1=[O:14]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 25517Ammonium ChlorideHCID 80170N-HydroxysuccinimideHCID 28184935-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 221477772-Tetralone-6-carboxamideYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tetralone-6-carboxylic acid, ethylene ketal (395 mg, 2.07 mmol) was co-dissolved in CH2Cl2 (50 mL) with N-hydroxysuccinimide (260 mg, 2.76 mmol) at 0° C. and treated with a slight excess of 1,3-dicyclohexylcarbodiimide (502 mg, 2.50 mmol). The mixture was allowed to warm to ambient temperature over 30 minutes, during which time a fine white precipitate formed. Ammonium chloride (333 mg, 6.23 mmol) and triethylamine (1.58 mL, 12.5 mmol, d=0.797) were added. The solution was stirred at ambient temperature for 16 hours. The suspended urea and salts were filtered away and the solution concentrated in vacuo to a colorless oil. The oil was applied to a silica flash chromatography column and eluted with 50-100% EtOAc in hexanes to yield 250 mg (64%) of 2-tetralone-6-carboxamide, ethylene ketal as a white solid, clean by NMR, TLC. 2-Tetralone-6-carboxamide ethylene ketal (250 mg, 1.07 mmol) and catalytic p-toluenesulfonic acid were stirred in acetone (50 mL) at ambient temperature for 48 hours. The volatiles were removed in vacuo and the residue triturated in ethyl acetate. The solids were filtered, washed and dried to yield 77.5 mg (38%) of 2-Tetralone-6-carboxamide as a white powder, pure by NMR, TLC. MS.

Workup

  1. customformed
  2. filtrationThe suspended urea and salts were filtered away
  3. concentrationthe solution concentrated in vacuo to a colorless oil
  4. washeluted with 50-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-5626a501ecff481da867abb729eba4c2
Source dataset
uspto-grants-2000_07
Patent number
US06093735

Reaction notes

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