Ammonia → HCID 10965854, compound

HRID 2205297Notes

Reaction equation

HRID 2205297 reaction equation
N.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C1C=CC2N(O)N=[N:24]C=2C=1.CCN=C=NCCCN(C)C.Cl>O1CCCC1>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([NH2:24])=[O:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 3015564'-Hydroxy-4-biphenylcarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 10965854HCID 10965854, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 50-mL round-bottom flask was placed tetrahydrofuran saturated with NH3 (gas) (20 mL), 4′-hydroxybiphenyl-4-carboxylic acid (1 g, 4.67 mmol, 1 equiv), HOBt (900 mg, 6.67 mmol, 1.4 equiv), EDCl (1.34 g, 7.0 mmol, 1.5 equiv). The resulting solution was stirred for 4 hrs at room temperature. The resulting mixture was concentrated under vacuum. The residue was dissolved in 50 mL of ethyl acetate, washed with 2×40 mL of H2O, 1×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The reside was purified by column chromatography on silica gel (eluting with 1:1 ethyl acetate/petroleum ether) to give 500 mg (50%) of 4′-hydroxybiphenyl-4-carboxamide as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. dissolutionThe residue was dissolved in 50 mL of ethyl acetate
  4. washwashed with 2×40 mL of H2O, 1×50 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe reside was purified by column chromatography on silica gel (eluting with 1:1 ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-5174fc68c4584027bb8a0579a6e9cd3b
Source dataset
uspto-grants-2016_06
Patent number
US09371285B2

Reaction notes

Loading…