4-Nitrobenzaldehyde → HCID 15516569, compound

HRID 2065964Notes

Reaction equation

HRID 2065964 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[N:12]=[C:13]([CH2:16][N:17]([CH3:27])C3C=CC(N(C)C)=CC=3)[S:14][CH:15]=2)[CH:8]=[C:7]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:6]=1[OH:32])([CH3:4])([CH3:3])[CH3:2].[N+:33]([C:36]1[CH:43]=[CH:42][C:39](C=O)=[CH:38][CH:37]=1)([O-:35])=[O:34].CO.[BH4-].[Na+]>O>[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[N:12]=[C:13]([CH2:16][NH:17][CH2:27][C:39]3[CH:42]=[CH:43][C:36]([N+:33]([O-:35])=[O:34])=[CH:37][CH:38]=3)[S:14][CH:15]=2)[CH:8]=[C:7]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:6]=1[OH:32])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 887MethanolHCID 4311764Sodium borohydrideHCID 9933557HCID 9933557, compound

Product 1

HCID 15516569HCID 15516569, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.5 g (1.57 mmol) of the compound of Example 9, 0.237 g (1.57 mmol) of 4-nitrobenzaldehyde and 1 g of previously activated pulverulent 4 Å molecular sieve are added successively to a flask containing 30 ml of anhydrous MeOH, under an inert atmosphere. The reaction mixture is vigorously stirred for 18 hours before the addition, by portions, of 0.06 g (1.57 mmol) of NaBH4. Stirring is maintained for another 4 hours before the addition of 5 ml of water. After a quarter of hour, the sieve is filtered out and the reaction mixture is extracted with two times 100 ml of CH2Cl2. The organic phase is washed successively with 50 ml of water then with 50 ml of salt water, dried over sodium sulphate, filtered and concentrated under vacuum. The residue is purified on a silica column (eluent: 50% ethyl acetate in heptane). A yellow oil is obtained with a yield of 55%.

Workup

  1. filtrationAfter a quarter of hour, the sieve is filtered out
  2. extractionthe reaction mixture is extracted with two times 100 ml of CH2Cl2
  3. washThe organic phase is washed successively with 50 ml of water
  4. dry with materialwith 50 ml of salt water, dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified on a silica column (eluent: 50% ethyl acetate in heptane)
  8. customA yellow oil is obtained with a yield of 55%

Sources & evidence

ORD record
ord-851bbbd6ca094950a3f6cb6f092740d4
Source dataset
uspto-grants-2012_10
Patent number
US08288560B2

Reaction notes

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