Sodium borohydride → HCID 178521538, compound

HRID 1895571Notes

Reaction equation

HRID 1895571 reaction equation
[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][C:21]2[C:4](=[CH:5][C:6]3[C:7](=[O:28])[C:8]4[C:17]([C:18](=[O:25])[C:19]=3[CH:20]=2)=[CH:16][C:15]2[C:10](=[CH:11][C:12]([Cl:27])=[C:13]([Cl:26])[CH:14]=2)[CH:9]=4)[CH:3]=1.[BH4-].[Na+]>CO>[OH:28][C@H:7]1[C:8]2[C:17](=[CH:16][C:15]3[C:10]([CH:9]=2)=[CH:11][C:12]([Cl:27])=[C:13]([Cl:26])[CH:14]=3)[C@H:18]([OH:25])[C:19]2[CH:20]=[C:21]3[C:4]([CH:3]=[C:2]([Cl:1])[C:23]([Cl:24])=[CH:22]3)=[CH:5][C:6]1=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 582891062,3,9,10-Tetrachloro-6,13-pentacenequinone

Product 1

HCID 178521538HCID 178521538, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2,3,9,10-tetrachloro-6,13-pentacenequinone (1.0 g, 2.24 mmol) in dry MeOH (40 mL) at 0° C. under an argon atmosphere was slowly added NaBH4 (0.85 g, 22.47 mmol). The reaction mixture was stirred at 0° C. for 0.5 h and at RT for 16 h, and then quenched with H2O at 0° C. The resulting mixture was filtered and washed with H2O and dried in vacuo to give product as a brown solids (0.92 g, 90%) which was identified as mixture of two isomers. 1H NMR (500 MHz, DMSO-d6): δ 8.36 (s, 4H), 8.16 (s, 4H), 6.82 (d, 2H), 5.82 (d, 2H). 1H NMR (500 MHz, DMSO-d6): δ 8.35 (s, 4H), 8.13 (s, 4H), 6.30 (d, 2H), 5.99 (d, 2H). LDI-MS m/z: 449.96[M+], 431[M+-OH], 415.97 [M+-2(OH)].

Workup

  1. customquenched with H2O at 0° C
  2. filtrationThe resulting mixture was filtered
  3. washwashed with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-38e3fdb5d4dd4a299a85c435f1a34d73
Source dataset
uspto-grants-2013_08
Patent number
US08513466B2

Reaction notes

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