Isatoic Anhydride → 2-Amino-N-(prop-2-yn-1-yl)benzamide

HRID 1616740Notes

Reaction equation

HRID 1616740 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[C:5]12[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH:10]C(=O)[O:8][C:6]2=O>CN(C=O)C.O.C(Cl)Cl>[NH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:5]=1[C:6]([NH:4][CH2:1][C:2]#[CH:3])=[O:8]

Participants

6

Reactant 2

HCID 8359Isatoic AnhydrideHCID 239041Propargylamine

Product 1

HCID 27644242-Amino-N-(prop-2-yn-1-yl)benzamideYield 51%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

A solution of propargylamine (1.00 mL, 14.6 mmol) in DMF (4.0 mL) was added dropwise to a solution of isatoic anhydride (1.57 g, 9.72 mmol) in DMF (8.0 mL) at 45° C. The solution was stirred at 45° C. for 16 h and diluted with water and CH2Cl2. The aqueous phase was extracted with CH2Cl2 washed with water, brine, dried and concentrated. The crude product was recrystallised from EtOAc/petrol to give 2-amino-N-propargylbenzamide (0.85 g, 51%) as a colourless solid; mp 100-101° C., lit. [29] 98-100° C.; δH (400 MHz, DMSO-d6) 3.08 (t, J=2.4 Hz, 1H, C≡CH), 3.97 (dd, J=5.6, 2.4 Hz, 2H, CH2), 6.45 (s, 2H, NH2), 6.49 (t, J4,5=J5,6=7.8 Hz, 1H, H5), 6.68 (d, J3,4=7.8 Hz, 1H, H3), 7.13 (t, J3,4=J4,5=7.8 Hz, 1H, H4), 7.46 (d, J5,6=7.8 Hz, 1H, H6), 6.61 (t, J=5.6 Hz, 1H, NH).

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2
  2. washwashed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was recrystallised from EtOAc/petrol

Sources & evidence

ORD record
ord-ec40a4365a3c410ab2198380f2d42b9c
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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