Methanol → HCID 131718220, compound

HRID 1656139Notes

Reaction equation

HRID 1656139 reaction equation
CO.[BH4-].[Na+].[N+:5]([N:8]1[C:12]2=[C:13]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C:14]3[CH:15]=[CH:16][C:17]([N:52]=3)=[C:18]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:19]3[N:23]([N+:24]([O-])=O)[C:22]([C:27]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[C:28]4[N:39]=[C:31]([C:32]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[C:9]1[CH:10]=[CH:11]2)[CH:30]=[CH:29]4)=[CH:21][CH:20]=3)([O-])=O>[Pd].ClCCl>[NH2:24][N:23]1[C:19]2=[C:18]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:17]3[CH:16]=[CH:15][C:14]([N:52]=3)=[C:13]([C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[C:12]3[N:8]([NH2:5])[C:9]([C:32]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[C:31]4[N:39]=[C:28]([C:27]([C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=5)=[C:22]1[CH:21]=[CH:20]2)[CH:29]=[CH:30]4)=[CH:10][CH:11]=3

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydride2×HCID 129713539HCID 129713539, compound

Product 1

HCID 131718220HCID 131718220, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A 2-1 three-necked round bottomed flask was fitted with a condenser and a dropping funnel to add solid material. To this flask was added anhydrous dichloromethane (850-ml) and methanol (420-ml). To this organic solution was added 10% palladium on carbon (14.0 g), the mixture was stirred under an argon blanket, and then cooled in an ice bath. Sodium borohydride (4.0 g, mol) was added in small portions over about 30-min. Next the dinitrotetraphenylporphyrin (7.0 g, 0.01 mol) and solid sodium borohydride (14.0 g) were added in small portions over about 60-min. The reaction mixture was stirred under argon for 30 min. The reaction mixture was filtered through a layer of CELITE® (diatomateous earth of Johns Manville, Denver, Colo.) in a Buchner funnel and washed repeatedly with dichloromethane. The solvent was completely removed under reduced pressure to produce a crude residue. The residue was redissolved in dry dichloromethane to separate insoluble CELITE®, and filtered. The solvent was removed under reduced pressure and dried to produce a purified residue (6.2 g). This residue was flash chromatographed over silica using dichloromethane as eluent. The product obtained (0.6 g, 9.6% yield) was free of impurities. See FIG. 4.

Workup

  1. customA 2-1 three-necked round bottomed flask was fitted with a condenser and a dropping funnel
  2. additionto add solid material
  3. temperaturecooled in an ice bath
  4. stirringThe reaction mixture was stirred under argon for 30 min
  5. filtrationThe reaction mixture was filtered through a layer of CELITE® (diatomateous earth of Johns Manville, Denver, Colo.) in a Buchner funnel
  6. washwashed repeatedly with dichloromethane
  7. customThe solvent was completely removed under reduced pressure
  8. customto produce a crude residue
  9. customto separate insoluble CELITE®
  10. filtrationfiltered
  11. customThe solvent was removed under reduced pressure
  12. customdried

Sources & evidence

ORD record
ord-bf84e23671c74289b81a7647498676a4
Source dataset
uspto-grants-1993_10
Patent number
US05252698

Reaction notes

Loading…