Dimethylformamide → HCID 23448413, compound

HRID 1838786Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:15]([OH:17])=[O:16].[N:18]12CCCN=C1C[CH2:22][CH2:21][CH2:20][CH2:19]2.BrCCCC#N.CN(C)C=O>O>[C:19]([CH2:20][CH2:21][CH2:22][O:16][C:15]([C:3]1[CH:4]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)[CH:6]=[CH:7][C:2]=1[OH:1])=[O:17])#[N:18]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 4,4′-dihydroxy-3-biphenylcarboxylic acid (2.3 g; 10 mmol), 1,8-diaza-bicyclo[5.4.0]undec-7-ene (1.7 g; 11.2 mmol), 4-bromobutyronitrile (1.7 g; 11.2 mmol) and N,N-dimethylformamide (40 ml) was heated at 75° C. for 4 h. The reaction mixture was cooled, poured into water (300 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with 1N-hydrochloric acid (150 ml) and with water (2×100 ml), dried over magnesium sulphate and filtered. The organic solvent was removed in vacuo. The residue (3.0 g) was purified by flash chromatography using a silica gel column and toluene/ethyl acetate (97:3) as eluent to give 2.1 g (70%) of 3-cyanopropyl-4,4′-dihydroxy-3-biphenylcarboxylate.

Workup

temperatureThe reaction mixture was cooled
extractionextracted with ethyl acetate (3×100 ml)
washThe combined organic layers were washed with 1N-hydrochloric acid (150 ml) and with water (2×100 ml)
dry with materialdried over magnesium sulphate
filtrationfiltered
customThe organic solvent was removed in vacuo
customThe residue (3.0 g) was purified by flash chromatography

Sources & evidence

ORD record: ord-2886ad5849364beb97265f158bb7008f
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06676851B1

Reaction notes

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