Diethyl Ether → HCID 59016629, compound

HRID 339462Notes

Reaction equation

HRID 339462 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([NH:8][NH2:9])=[O:7].[CH2:14]1[C:23](=O)[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1.CCOCC>CO.C(O)(=O)C>[CH2:20]1[C:21]2[C:16](=[CH:15][CH:14]=[CH:23][CH:22]=2)[CH2:17][CH2:18][C:19]1=[N:9][NH:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[C:4]=1[CH3:13]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 682662-TetraloneHCID 450912733-Methoxy-2-methylbenzohydrazide

Product 1

HCID 59016629HCID 59016629, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

3-Methoxy-2-methyl-benzoic acid hydrazide (1.0 g) and β-tetralone (0.9 g) were mixed in 4 ml of methanol with 1 drop of acetic acid at room temperature for 10 minutes. Approximately 10 mL of ether were added and the mixture was refrigerated. Crystals of 3-methoxy-2-methyl-benzoic acid (3,4-dihydro-1H-naphthalen-2-ylidene)-hydrazide formed, which were collected by filtration (0.85 g). 1H NMR (300 MHz, CDCl3) δ ppm): 6.8-7.3 (m, 4H), 3.75+3.8 (2 s, 3H), 3.45+3.7 (2 s, 2H), 2.85 (t, 2H), 2.4 (t, 2H), 2.27+2.25 (2 s, 3H); multiple conformers; Rf=0.56 (3:1 ethyl acctate:hexane); m.p.=138° C.; m.p. of 3-methoxy-2-methyl-benzoic acid hydrazide=113-116° C.

Sources & evidence

ORD record
ord-1dd47cbce55e4c00928b144a3c29bf0f
Source dataset
uspto-grants-2014_11
Patent number
US08895306B2

Reaction notes

Loading…