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Chemical Structure| 119-68-6 Chemical Structure| 119-68-6

Structure of 2-(Methylamino)benzoic acid
CAS No.: 119-68-6

Chemical Structure| 119-68-6

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Product Details of [ 119-68-6 ]

CAS No. :119-68-6
Formula : C8H9NO2
M.W : 151.16
SMILES Code : O=C(O)C1=CC=CC=C1NC
MDL No. :MFCD00002424
InChI Key :WVMBPWMAQDVZCM-UHFFFAOYSA-N
Pubchem ID :67069

Safety of [ 119-68-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 119-68-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 119-68-6 ]

[ 119-68-6 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 119-68-6 ]
  • [ 57-13-6 ]
  • [ 604-50-2 ]
YieldReaction ConditionsOperation in experiment
64.3% at 150℃; for 5h; Urea (460 mmol) was heated to melt, then 2-methylaminobenzoic acid (46 mmol) was added. The mixture was stirred for 5 h at 150 C and then cooled to below 100 C. Water (70 mL) was added to quench the reaction. The precipitated was collected and recrystallized in a mixed solution of acetone (10 mL) and water (100 mL) to afford compound 1 as a white powder (5.25 g, 64.3%); mp 278-279 C; 1H NMR (DMSO-d6) delta (ppm): 3.43 (s, 3H), 7.26 (t, J = 12 Hz, 1H), 7.41 (d, J = 12 Hz, 1H), 7.75 (t, J = 15 Hz, 1H), 7.98 (d, J = 6 Hz, 1H), 11.54 (s, 1H). ESI-MS (m/z): 177 (M+H)+.
  • 3
  • [ 119-68-6 ]
  • [ 150374-99-5 ]
  • [ 188115-02-8 ]
  • 4
  • [ 119-68-6 ]
  • [ 917-61-3 ]
  • [ 604-50-2 ]
YieldReaction ConditionsOperation in experiment
84% With acetic acid; sodium hydroxide; In water; at 75℃; for 4h; Sodium cyanate (28mmol) in water (25mL) was added to a solution of N-methyl anthranilic acid (20mmol) and acetic acid (0.2mL) in water (50mL) with stirring. When the temperature of the reaction mixture reached 40C, NaOH was added in portions till the reaction temperature reach to 75C. Stirring was continued without cooling for 4h, after which the crystals were filtered off and dissolved in boiling water (50mL). The solution was acidified with 50% H2SO4 to pH 1-2. The precipitated crystals were filtered off, washed with water and recrystallized from 50% acetic acid to give compound 2 (2.92g, 84%); m p 278C [24].
77% Sodium cyanate (30.15 g, 0.46 mol) was added to a slurry of N- methylanthranilic acid (50.0 g, 0.33 mol) in water (1 .75 L) and acetic acid (3.3 mL). The reaction mixture was heated to 50 C for 1 h. The solution was slowly basified by the addition of sodium hydroxide (exothermic). The resulting solution was heated to 80 C and stirred overnight. The reaction mixture was cooled to 0 C and the resultant precipitate collected by filtration. The solid was dissolved in boiling water (200 mL) and acidified with cone, sulfuric acid to pH 2. The slurry was cooled to room temperature and filtered. The solid was dried in a vacuum oven to give 1 -methylquinazoline-2,4(1 H,3H)-dione (53 g, 0.30 mol, 77%).1 H NMR (300MHz, DMSO-d6) delta = 1 1 .54 (br. s., 1 H), 8.00 (d, J = 7.7 Hz, 1 H), 7.77 (t, J = 7.9 Hz, 1 H), 7.43 (d, J = 8.6 Hz, 1 H), 7.28 (t, J = 7.5 Hz, 1 H), 3.33 (s, 3H)
69% With acetic acid; sodium hydroxide; In water; at 40 - 75℃; for 4h; 2-(Methylamino)benzoic acid (4.50 g, 0.0300 mol) and acetic acid (0.3 mL) were dissolved in water (158 mL), a solution of sodium isocyanate (2.76 g, 42.0 mmol) in water (54 mL) was added slowly at room temperature. The reaction mixture was heated to 40C and added with sodium hydroxide (34.8 g, 0.870 mol). The temperature was raised to 75C and the reaction solution was stirred for 4 hours, cooled to room temperature, filtered and the filter cake was dissolved in boiling water (10 mL). The system was adjusted to pH 1-2 with 50% sulfuric acid solution (15 mL), filtered and the filter cake was washed with a small amount of water (3 mL) and dried under reduced pressure to give 1-methylquinazoline-2,4-dione (3.64 g, as a yellow solid) with a yield of 69%. 1H NMR: (400 MHz, DMSO-d6) delta 11.55(s, 1H), 8.00(d, J = 8.0 Hz, 1H), 7.78(t, J = 8.0 Hz, 1H), 7.42(d, J = 8.0 Hz, 1H), 7.28(t, J = 8.0 Hz, 1H), 3.44(s, 3H). MS-ESI calcd. [M + H]+ 177, found 177.
  • 5
  • [ 3382-18-1 ]
  • [ 119-68-6 ]
  • 2,3-dimethoxy-13-methyl-5,6,13,13a-tetrahydro-8H-isoquinolino[1,2-b]quinazolin-8-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In toluene; at 90℃; for 20h; General procedure: To a solution of imine (1 mmol) and acid (1.2 mmol) in dry toluene (10 mL) was added sequentially DIPEA (1.85 mmol) andthen T3P (1.5 mmol, 50% in THF). The resulting solution was heatedat 90C or 120C in a sealable tube for the specified time, before cooling to RT and pouring into satd aq NaHCO3 (20 mL). The aqueous layer was extracted with DCM (330 mL), concentrated in vacuo and purified by column chromatography.
  • 6
  • [ 24424-99-5 ]
  • [ 119-68-6 ]
  • [ 141871-02-5 ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine; In acetonitrile; at 20℃; for 2h; General procedure: To a solution of anthranilic acid (0.5g, 3.64mmol) in acetonitrile (10mL) were added TEA (0.73g, 7.28mmol), Boc anhydride (0.95g, 4.37mmol), and DMAP (0.044g, 0.36mmol). The mixture was stirred at rt for 2.0 h. CMPI (1.1g, 4.36mmol) was added in one lot to the reaction mixture. The reaction mixture was stirred at rt for 10 min. 1N HCl (20mL) was added to the reaction and the mixture was extracted two times with EtOAc. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting solid was crystallized in DCM and MeOH to afford 0.56g (95%) of 1H-benzo[d][1,3]oxazine-2,4-dione as an off white solid. 1H NMR (400MHz, DMSO) δ 7.14-7.16 (d, J=8Hz, 1H), 7.23-7.27 (t, J=16Hz,1H), 7.72-7.74 (t, J=8Hz, 1H), 7.90-7.92 (d, J=8Hz,1H), 11.72 (s, 1H). 13C NMR (100MHz, DMSO-d6) δ 110.6, 115.7, 123.9, 129.3, 137.3, 141.8, 147.5, 160.3. IR (thin film) 3461, 3173, 2937, 1984, 1753, 1604, 1486, 1358, 1258, 1138, 1009, 765, 673, 492. ES-MS (m/z): 161.8 (M+-H). MP (C): 236.
 

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