Diethyl Ether → HCID 59016629, compound

HRID 968933Notes

Reaction equation

HRID 968933 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].CCO[CH2:17][CH3:18]>CO.C(O)(=O)C>[CH2:6]1[C:17]2[C:18](=[CH:12][CH:3]=[CH:4][CH:13]=2)[CH2:11][CH2:10][C:5]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

5

Reactant 2

HCID 3283Diethyl EtherHCID 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 P-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 acetate:hexane); m.p.=138° C.; m.p. of 3-methoxy-2-methyl-benzoic acid hydrazide=113-116° C.

Sources & evidence

ORD record
ord-0703aa85c8764ec3aa46ab81a9952377
Source dataset
uspto-grants-2007_12
Patent number
US07304162B2

Reaction notes

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