3-Hydroxy-2-naphthoic acid hydrazide → HCID 52950904, compound

HRID 1896344Notes

Reaction equation

HRID 1896344 reaction equation
[OH:1][C:2]1[C:3]([C:12]([NH:14][NH2:15])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[N+:16]([C:19]1[O:23][C:22](/[CH:24]=[CH:25]/[CH:26]=O)=[CH:21][CH:20]=1)([O-:18])=[O:17]>C(O)(=O)C>[OH:1][C:2]1[C:3]([C:12]([NH:14]/[N:15]=[CH:26]/[CH:25]=[CH:24]/[C:22]2[O:23][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=2)=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 726993-Hydroxy-2-naphthoic acid hydrazideHCID 54629625-Nitrofuryl-2-acrolein

Product 1

HCID 52950904HCID 52950904, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic acid (3 mL) is added to a mixture of 3-Hydroxy-2-naphthoic acid hydrazide (100 mg, 0.50 mmol) and (E)-3-(5-nitrofuran-2-yl)acrylaldehyde (99 mg, 0.59 mmol) and the resulting mixture is stirred for 2 h (Note: Immediate precipitation of the yellowish hydrazone product is observed after which the reaction mixture is stirred for another 2 h for completion). The reaction mixture is then diluted with 50% ether/hexanes. The yellowish solid is filtered with suction, washed with 50% ether/hexanes (100 mL) and dried to furnish 172 mg (99%) of the desired product as a yellowish solid. m. p. 259° C. 1H NMR (DMSO) δ 12.00 (br s, 1H), 11.3 (br s, 1H), 8.42 (s, 1H), 8.25 (d, 1H, J=8.1 Hz), 7.91 (d, 1H, J=8.4 Hz), 7.86-7.66 (m, 2H), 7.58-7.45 (m, 1H), 7.42-7.29 (m, 1H), 7.32 (s, 1H) and 7.25-7.06 (m, 3H); 13C NMR (DMSO) δ 163.7, 154.8, 153.8, 151.4, 148.5, 135.9, 130.5, 130.4, 128.7, 128.3, 126.8, 125.8, 124.3, 123.8, 120.5, 115.4, 113.6 and 110.5.

Workup

  1. customImmediate precipitation of the yellowish hydrazone product
  2. stirringis stirred for another 2 h for completion)
  3. additionThe reaction mixture is then diluted with 50% ether/hexanes
  4. filtrationThe yellowish solid is filtered with suction
  5. washwashed with 50% ether/hexanes (100 mL)
  6. customdried

Sources & evidence

ORD record
ord-b15865fc1aec4fda8684cf8aaf49cb05
Source dataset
uspto-grants-2013_08
Patent number
US08518968B2

Reaction notes

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