4-Hydroxybenzaldehyde → HCID 58043115, compound

HRID 1035240Notes

Reaction equation

CS([O:5][CH:6]1[CH2:9][N:8]([C:10]([C:12]2[O:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][N:16]=2)=[O:11])[CH2:7]1)(=O)=O.O[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CC(N(C)C)=O>[C:17]1([C:14]2[O:13][C:12]([C:10]([N:8]3[CH2:9][CH:6]([O:5][C:24]4[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=4)[CH2:7]3)=[O:11])=[N:16][N:15]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Intermediate 53B (5.0 g, 15.5 mmol) was dissolved in DMA (40 mL) and 4-hydroxybenzaldehyde (2.17 g, 17.8 mmol) was added followed by Cs2CO3 (5.8 g, 17.8 mmol). The mixture was stirred at 110° C. for 5 h. Water was added and the mixture was extracted trice with DCM. The solution was filtered through a phase separator and the solvent was removed by evaporation. Ether was added to the residue and the formed solid was filtered and washed with ether. The product was dried in vacuo to give 3.58 g (66%) of 71A as a beige solid. 1H NMR (500 MHz, CDCl3): δ 4.37 (m, 1H), 4.70 (m, 1H), 4.79 (m, 1H), 5.18 (m, 2H), 6.91 (d, 2H), 7.53 (t, 2H), 7.60 (t, 1H), 7.87 (d, 2H), 8.16 (d, 2H), 9.92 (s, 1H).

Workup

extractionthe mixture was extracted trice with DCM
filtrationThe solution was filtered through a phase separator
customthe solvent was removed by evaporation
additionEther was added to the residue
filtrationthe formed solid was filtered
washwashed with ether
customThe product was dried in vacuo

Sources & evidence

ORD record: ord-d57330169b324064a880f5c671d19ecc
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546375B2

Reaction notes

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