Acetic Acid → 6,7-Dihydroxy-3-(2H-tetrazol-5-yl)-chromen-2-one

HRID 965786Notes

Reaction equation

HRID 965786 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([OH:11])=[CH:6][C:3]=1[CH:4]=O.C([O:14][C:15](=O)[CH2:16][C:17]1[N:18]=[N:19][NH:20][N:21]=1)C.N1CCCCC1.C(O)(=O)C>CN(C=O)C>[OH:11][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][C:8]=1[OH:10])[O:1][C:15](=[O:14])[C:16]([C:17]1[N:18]=[N:19][NH:20][N:21]=1)=[CH:4]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 543616Ethyl 1H-tetrazole-5-acetateHCID 6433872,4,5-Trihydroxybenzaldehyde

Product 1

HCID 1358479506,7-Dihydroxy-3-(2H-tetrazol-5-yl)-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,4,5-trihydroxybenzaldehyde (1.23 g), (2H-tetrazol-5-yl)-acetic acid ethyl ester (1.25 g), piperidine (1.36 g) and acetic acid (0.06 g) in DMF (10 ml) was stirred at 90° C. under nitrogen for two hours. After ice water treatment and acidification to pH 2 the product was filtered and triturated with hot ethanol. Yield: 0.55 g.

Workup

  1. filtrationAfter ice water treatment and acidification to pH 2 the product was filtered
  2. customtriturated with hot ethanol

Sources & evidence

ORD record
ord-e5f95f22bf53429da2557a2b5f27f8cf
Source dataset
uspto-grants-2005_10
Patent number
US06951870B2

Reaction notes

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