Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1) → HCID 22462810, compound

HRID 1936837Notes

Reaction equation

HRID 1936837 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:15])([CH3:14])[CH2:9][C:10]2=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH:17]([C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([OH:23])=[O:22])N>C(O)=O>[CH3:14][C:8]1([CH3:15])[C:9]2[C:27]3[C:19](=[C:20]([C:21]([OH:23])=[O:22])[CH:24]=[CH:25][CH:26]=3)[NH:17][C:10]=2[C:11]2[C:7]1=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2

Participants

4

Reactant 2

HCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)HCID 124417863,3-dimethyl-6-nitro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 22462810HCID 22462810, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

6-Nitro-3,3-dimethyl-1-indanone (0.612 g, 2.98 mmol) [Smith, J. G. et al. Org. Prep. and Proc. Int. 1978, 10(3), 123-131] and 2-hydrazinobenzoic acid hydrochloride (0.562 g, 2.98 mmol) in formic acid (2 mL, 96%) were irradiated for two minutes in a closed cap Teflon vessel of a microwave oven (700W). The mixture was vacuum filtered, and the crude product was chromatographed (hexane/ethyl acetate 1:1) and triturated with petroleum ether/diethyl ether. Drying in vacuo afforded 0.178 g (19%) of the title compound as a yellow solid: mp 310° C. (dec); 1H NMR (DMSO-d6): δ 13.43 (s, 1H), 11.85 (s, 1H), 8.95 (s, 1H), 8.12 (d, 1H), 7.98 (d, 1H), 7.81 (m, 2H), 7.19 (t, 1H), 1.59 (s, 6H); IR (KBr): 3460, 1670 cm−1; MS (m/z) 322 (M+).

Workup

  1. filtrationfiltered
  2. customthe crude product was chromatographed (hexane/ethyl acetate 1:1)
  3. customtriturated with petroleum ether/diethyl ether
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-b383cf5ede2d4eee88b6eb71ea47084b
Source dataset
uspto-grants-2002_05
Patent number
US06391902B1

Reaction notes

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