Ethanol → 4'-(Aminomethyl)-biphenyl-2-carboxylic acid 1,1-dimethylethyl ester

HRID 1742102Notes

Reaction equation

HRID 1742102 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2C(=O)C3=CC=CC=C3C2=O)=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN.C(O)C>C(Cl)Cl>[NH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 10024731N-[[2'-(t-butoxycarbonyl)biphenyl-4-yl]methyl]phthalimide

Product 1

HCID 99710734'-(Aminomethyl)-biphenyl-2-carboxylic acid 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.62 g (6.35 mmole) of N-[[2'-(t-butoxycarbonyl)biphenyl-4-yl]methyl]phthalimide, 1.21 ml (1.25 g, 25 mmole) of 100% hydrazine hydrate, and 35 ml of absolute ethanol was stirred at room temperature for 7.5 hours. During this time all of the solid gradually dissolved, followed by precipitation. Glacial acetic acid (3.7 ml) was added, and stirring was continued overnight. The white solid was then removed by filtration, and the filtrate was concentrated at room temperature. The residual oil was taken up in 100 ml of ether and washed with 2×50 ml of saturated aqueous Na2CO3 solution. Next, the product was extracted by shaking the ethereal solution with 50 ml of 0.5 N HCl. The aqueous layer was separated and basified by addition of excess saturated Na2CO3. The product, which oiled out, was extracted with 100 ml of ether. The ether phase was dried (Na2SO4), filtered, and concentrated at 30° C. to give 1.58 g (88%) of a very pale yellow, viscous oil, homogeneous by TLC in 95:5:0.5 CH2Cl2 --MeOH-concd NH40H.

Workup

  1. dissolutionDuring this time all of the solid gradually dissolved
  2. customfollowed by precipitation
  3. additionGlacial acetic acid (3.7 ml) was added
  4. stirringstirring
  5. waitwas continued overnight
  6. customThe white solid was then removed by filtration
  7. concentrationthe filtrate was concentrated at room temperature
  8. washwashed with 2×50 ml of saturated aqueous Na2CO3 solution
  9. extractionNext, the product was extracted
  10. stirringby shaking the ethereal solution with 50 ml of 0.5 N HCl
  11. customThe aqueous layer was separated
  12. additionbasified by addition of excess saturated Na2CO3
  13. extractionwas extracted with 100 ml of ether
  14. dry with materialThe ether phase was dried (Na2SO4)
  15. filtrationfiltered
  16. concentrationconcentrated at 30° C.
  17. customto give 1.58 g (88%) of a very pale yellow, viscous oil

Sources & evidence

ORD record
ord-ddb0eca6a51846e5874114e9209efb89
Source dataset
uspto-grants-1994_08
Patent number
US05336778

Reaction notes

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