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Product Details of 4-Amino-3-hydroxybenzoic acid

CAS No. :2374-03-0
Formula : C7H7NO3
M.W : 153.14
SMILES Code : C1=C(O)C(=CC=C1C(=O)O)N
MDL No. :MFCD00017094
InChI Key :NFPYJDZQOKCYIE-UHFFFAOYSA-N
Pubchem ID :137566

Safety of 4-Amino-3-hydroxybenzoic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4-Amino-3-hydroxybenzoic acid

* 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.

  • Upstream synthesis route of [ 2374-03-0 ]
  • Downstream synthetic route of [ 2374-03-0 ]

[ 2374-03-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1445-45-0 ]
  • [ 2374-03-0 ]
  • [ 13452-14-7 ]
YieldReaction ConditionsOperation in experiment
100% at 100℃; for 0.0833333 h; Microwave irradiation A heterogeneous mixture of 4-amino-3-hydroxybenzoic acid (7b) (7.732 g, 0.050 mol) and 1,1,1-trimethoxyethane (16 mL) was heated to 100 °C using a microwave (55 W) and held for 5 min. The reaction was repeated two more times (7.732 g and 7.625 g), and the combined reaction mixtures were concentrated in vacuo giving the product as a tan solid in quantitative yield: mp 245–246 °C (lit.40 245–246 °C); TLC (SiO2, ethyl acetate/methanol (90:10), UV) single spot Rf 0.38; MS MH+ 178.4. 1H NMR (300 MHz, DMSO); δ 2.66 (s, 3H, NCH3), 7.75 (d, J = 8.3 Hz, 1H, H-5), 7.96 (dd, J = 8.3, 1.4 Hz, 1H, H-7), 8.16 (d, J = 0.7 Hz, 1H, H-7), 13.12 (bs, 1H, OH).
95% at 100℃; for 0.0833333 h; Microwave irradiation A solution of compound 4.1 (1.10 g) and 1,1,1-trimethoxyethane (5 mL) was heated at 100° C. for 5 minutes in a microwave. The reaction mixture was concentrated under reduced pressure to provide 1.26 g of compound 4.2 (95percent pure) as a brown powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.66 (s, 3H), 7.74 (d, J=8.4 Hz, 1H), 7.96 (dd, J=8.3, 1.4 Hz, 1H), 8.16 (d, J=1.4 Hz, 1H), 13.07 (s(br), 1H).
References: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6661 - 6664.
[2] Patent: US2010/305073, 2010, A1, . Location in patent: Page/Page column 20.
[3] Patent: US2003/73707, 2003, A1, .
[4] Patent: EP1229027, 2002, A1, . Location in patent: Page 18.
[5] Patent: EP1229028, 2002, A1, . Location in patent: Page 18.
[6] Patent: EP1229037, 2002, A1, . Location in patent: Page 18.
[7] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4998 - 5002.
[8] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3242 - 3253.
  • 2
  • [ 64-19-7 ]
  • [ 2374-03-0 ]
  • [ 13452-14-7 ]
YieldReaction ConditionsOperation in experiment
62% at 130℃; for 72 h; (Intermediate Example 70)
2-Methylbenzoxazole-6-carboxylic acid
4-Amino-3-hydroxybenzoic acid (4.9 g) was added to acetic acid (250 ml) and stirred for 3 days at 130°C.
The solution was concentrated under reduced pressure, and precipitates were collected by filtration.
The precipitates were dissolved in methanol and chloroform.
The solution was concentrated under reducedpressure, and precipitates were collected by filtration, washed with methanol and dried under reduced pressure to give the title compound (3.5 g, Y.: 62percent).
1H NMR; (DMSO-d6) δ (ppm): 2.6 (s, 3H), 7.7 (d, 1H), 7.9 (dd, 1H), 8.1 (d, 1H).
ESI/MS (m/z): 178 (M+H)+, 176 (M-H)-.
References: [1] Patent: EP1595866, 2005, A1, . Location in patent: Page/Page column 27.
 

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