Hydrazine hydrate (1:1) → 2'-Aminomethylbiphenyl-2-carboxylic acid

HRID 1014076Notes

Reaction equation

HRID 1014076 reaction equation
C1(=O)[N:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[C:14]([C:19]([OH:21])=[O:20])=[CH:15][CH:16]=[CH:17][CH:18]=2)C(=O)C2=CC=CC=C12.O.NN>CO>[NH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[C:14]([C:19]([OH:21])=[O:20])=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 142585712'-Phthalimidomethylbiphenyl-2-carboxylic acid

Product 1

HCID 155093832'-Aminomethylbiphenyl-2-carboxylic acidYield 75.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 10.0 g (28 mmol) of 2′-phthalimidomethylbiphenyl-2-carboxylic acid in 450 ml of methanol was treated with 20 ml of hydrazine hydrate and heated at 40° C. for 1.5 h. The reaction mixture was concentrated and the residue was taken up in 250 ml of methylene chloride. After filtering off undissolved 2,3-dihydrophthalazine-1,4-dione, the mother liquor was concentrated and 4.8 g of 2′-aminomethylbiphenyl-2-carboxylic acid were obtained.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationAfter filtering off undissolved 2,3-dihydrophthalazine-1,4-dione
  3. concentrationthe mother liquor was concentrated

Sources & evidence

ORD record
ord-3bf8709e623b494d89e7081f39f7d8d5
Source dataset
uspto-grants-2011_07
Patent number
US07982045B2

Reaction notes

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