Ethyl 4-bromobutyrate → Ethyl 4-(6-methoxybiphenyl-3-yl)aminobutyrate

HRID 1389225Notes

Reaction equation

HRID 1389225 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.C(N(C(C)C)C(C)C)C.Br[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(OCC)C>[CH3:15][O:14][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:7][C:2]([NH:1][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 76300Ethyl 4-bromobutyrateHCID 81531DiisopropylethylamineHCID 1235414-Methoxy-3-phenylaniline

Product 1

HCID 20298363Ethyl 4-(6-methoxybiphenyl-3-yl)aminobutyrate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

29.5 g of 5-amino-2-methoxybiphenyl, 19.2 g of ethyldiisopropylamine and 28.9 g of ethyl 4-bromobutyrate are heated together (while stirring) for 4 hours at 125°. After cooling, the resulting reaction product is stirred with diethyl ether and filtered from the precipitated salt. The residue (remaining after evaporating off the ether) is recrystallized from isopropyl alcohol to obtain 22.5 g (48.5% of theory) of ethyl 4-(6-methoxybiphenyl-3-yl)amiobutyrate, MP 71° to 72.

Workup

  1. temperatureAfter cooling
  2. customthe resulting reaction product
  3. filtrationfiltered from the precipitated salt
  4. customafter evaporating off the ether)
  5. customis recrystallized from isopropyl alcohol
  6. customto obtain 22.5 g (48.5% of theory) of ethyl 4-(6-methoxybiphenyl-3-yl)amiobutyrate, MP 71° to 72

Sources & evidence

ORD record
ord-27be8e6e888b4915a49a0e136fae22c4
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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