Hydrochloric Acid → HCID 68997237, compound

HRID 1821416Notes

Reaction equation

HRID 1821416 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[N+:21]([O-])=O)=[N:2]1.[Sn].Cl>C(O)C>[NH2:21][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:12]=1[CH:11]=[CH:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1)[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 68998390HCID 68998390, compound

Product 1

HCID 68997237HCID 68997237, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude 4-[2-(1H-indazol-3-yl)vinyl]-3-nitrobenzoic acid (1.0 g, 3.2 mmol) obtained in Step 1 was dissolved in ethanol (30 mL) and the solution was added with tin (1.2 g, 9.7 mmol) and concentrated hydrochloric acid (7.0 mL), followed by reacting at 40° C. to obtain 3-amino-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid. The crude product (0.65 g, 2.3 mmol) was added with xylene (20 mL), triethylamine (0.16 mL, 1.2 mmol), phthalic anhydride (0.41 g, 2.8 mmol) and molecular sieves 3A (0.65 mg), followed by heating at 140° C. for 4 hours. The reaction mixture was filtered and the filtrate was acidified by hydrochloric acid (2 mol/L). The precipitated crystal was collected by filtration to obtain 3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid.

Workup

  1. customby reacting at 40° C.

Sources & evidence

ORD record
ord-35a5a459cd06453dab162f0053f30c4b
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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