33906-30-8|2-Hydrazineylbenzoic acid xhydrochloride| Ambeed

* 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 [ 33906-30-8 ]

[ 33906-30-8 ] Synthesis Path-Downstream 1~54

1
[ 122-31-6 ]
[ 33906-30-8 ]
[ 55317-53-8 ]

References: [1]Journal of the American Chemical Society,1958,vol. 80,p. 6271,6273.

2
[ 120-57-0 ]
[ 33906-30-8 ]
2-piperonylidenehydrazino-benzoic acid [ No CAS ]

References: [1]Dansk Tidsskrift for Farmaci,1940,vol. 14,p. 188.
Chem.Abstr.,1942,p. 2495.

3
[ 108-94-1 ]
[ 33906-30-8 ]
[ 65764-51-4 ]

References: [1]Journal of the Chemical Society,1926,p. 809.

4
[ 141-97-9 ]
[ 33906-30-8 ]
[ 109128-56-5 ]

References: [1]Justus Liebigs Annalen der Chemie,1910,vol. 373,p. 167.

5
[ 33906-30-8 ]
[ 7364-25-2 ]

References: [1]Chemische Berichte,1891,vol. 24,p. 795.

6
[ 33906-30-8 ]
[ 7364-25-2 ]

References: [1]Chemische Berichte,1921,vol. 54,p. 1115.
[2]Organic Syntheses,1949,vol. 29,p. 55.

7
[ 33906-30-8 ]
[ 100-52-7 ]
[ 4036-59-3 ]

References: [1]Chemische Berichte,1902,vol. 35,p. 2318.

8
[ 33906-30-8 ]
[ 17303-83-2 ]
[ 17303-90-1 ]

References: [1]Acta Chemica Scandinavica (1947),1967,vol. 21,p. 2151 - 2166.

9
[ 33906-30-8 ]
[ 25112-00-9 ]
[ 25112-09-8 ]

References: [1]Justus Liebigs Annalen der Chemie,1969,vol. 729,p. 139 - 145.

10
[ 2525-16-8 ]
[ 33906-30-8 ]
2-[N'-Azepan-(2Z)-ylidene-hydrazino]-benzoic acid; hydrochloride [ No CAS ]

References: [1]Pharmazie,1993,vol. 48,p. 410 - 414.

11
[ 99-49-0 ]
[ 33906-30-8 ]
carvone hydrazono-orthobenzoic acid [ No CAS ]

References: [1]Bulletin des Societes Chimiques Belges,1993,vol. 102,p. 39 - 52.

12
[ 10198-84-2 ]
[ 33906-30-8 ]
2-(2-Carboxyphenyl)-3-(pyridin-2-yl)-4,5,6,7-tetrahydroindazole [ No CAS ]

References: [1]Journal of Organic Chemistry,1994,vol. 59,p. 1761 - 1765.

13
[ 33906-30-8 ]
[ 123-06-8 ]
[ 124570-55-4 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 713 - 716.

14
[ 2648-51-3 ]
[ 33906-30-8 ]
2-{N'-[3,3-Dichloro-prop-2-en-(E)-ylidene]-hydrazino}-benzoic acid [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1990,vol. 26,p. 36 - 39.
Khimiya Geterotsiklicheskikh Soedinenii,1990,p. 42 - 45.

15
[ 4428-98-2 ]
[ 33906-30-8 ]
<1,2,4>Triazolo<1,5-a>chinazolin-5(4H)-on [ No CAS ]

References: [1]Helvetica Chimica Acta,1980,vol. 63,p. 1 - 9.
[2]Helvetica Chimica Acta,1980,vol. 63,p. 1 - 9.

16
[ 53557-77-0 ]
[ 33906-30-8 ]
(5-Oxo-4,5-dihydro<1,2,4>triazolo<1,5-a>chinazolin-2-yl)-acetonitrile [ No CAS ]

References: [1]Helvetica Chimica Acta,1980,vol. 63,p. 1 - 9.

17
[ 1558-82-3 ]
[ 33906-30-8 ]
[ 73549-69-6 ]

References: [1]Helvetica Chimica Acta,1980,vol. 63,p. 1 - 9.

18
[ 33906-30-8 ]
[ 98-88-4 ]
[ 83412-89-9 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 641 - 643.

19
[ 33906-30-8 ]
[ 122-04-3 ]
[ 83412-90-2 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 641 - 643.

20
[ 24424-99-5 ]
[ 33906-30-8 ]
[ 155290-47-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium carbonate; In 1,4-dioxane; water; at 0 - 20℃; for 24h;pH 8 - 9;	a) 2-[2-(tert-Butoxycarbonyl)hydrazino]benzoic acid (IV'A.1); To a solution of 3 g of <strong>[33906-30-8]2-hydrazinobenzoic acid hydrochloride</strong> (16 mmol, 1 eq.) in dioxane (1 mL/mmol) is added a solution of 3.81 g of Boc2O (17.5 mmol, 1.1 eq.) in dioxane (0.4 mL/mmol). The solution is cooled to 0 C. and aqueous 5% Na2CO3 solution is added dropwise to pH 8-9. The solution is then warmed to room temperature and stirring is continued for 24 hours. The dioxane is evaporated off. The medium is taken up in water and then acidified with 1N HCl solution to pH 1. The mixture is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and evaporated to dryness. The powder obtained is triturated with petroleum ether and then dried under vacuum to give 3.75 g of compound (IV'A.1) (yield 93%).1H NMR 300 MHz (DMSO): delta (ppm)=1.41 (s, 9H, C(CH3)3); 6.75 (t, J=7.5 Hz, 1H, H3); 6.86 (d, J=8.1 Hz, 1H, H5); 7.43 (t, J=7.8 Hz, 1H, H4); 7.81 (d, J=8.1 Hz, 1H, H6); 8.88 (s, 1H, NH); 9.05 (s, 1H, NH); 13 (s, 1H, COOH).IR (KBr): nuNH=3381.6 cm-1; nuCsp3-H=2971.7 cm-1; nuCO=1697.6 cm-1 and 1676.7 cm-1; nuCC=1609.1 cm-1 and 1587.2 cm-1.Melting point=146 C.
93%	With sodium carbonate; In 1,4-dioxane; water; at 20℃; for 24h;pH 8 - 9;	A solution of <strong>[33906-30-8]2-hydrazinobenzoic acid hydrochloride</strong>(l: l) (3.00 g, 15.9 mmol) in dioxane (55 ml) was treated with a solution of di-tert-butyl dicarbonate (3.8 g, 17 mmol) in dioxane (7 ml). The resulting solution was cooled to 0 C and the solution was adjust to pH 8-9 with an aqueous solution of sodium carbonate (5% w/w). The reaction mixture was stirred 24 h at room temperature. The dioxane was evaporated, the residue was retaken in water. The solution was brought to pH =1 with an aqueous solution of hydrogenchloride (IN). The mixture was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated. The resulting solid was triturated with petroleum ether, filtered off and dried under high vacuum affording 3.75 g (93 % of th.) of the title compound. LC-MS (Method 6): Rt = 1.07 min; MS (ESIneg): m/z = 251.2. [M-H]"

References: [1]Patent: US2012/10161,2012,A1 .Location in patent: Page/Page column 11.
[2]Patent: WO2019/81307,2019,A1 .Location in patent: Page/Page column 119-120.
[3]Journal of Medicinal Chemistry,1996,vol. 39,p. 1172 - 1188.

21
anthranilic acid-hydrochloride [ No CAS ]
[ 33906-30-8 ]

References: [1]Organic Syntheses,1949,vol. 29,p. 55.

22
[ 33906-30-8 ]
phosphorus oxychloride [ No CAS ]
[ 29110-74-5 ]

References: [1]Chemische Berichte,1901,vol. 34,p. 798.

24
[ 33906-30-8 ]
[ 1118-60-1 ]
5-amino-3-methyl-1-o-carboxyphenylpyrazole [ No CAS ]