Dimethylformamide → HCID 23153963, compound

HRID 1175789Notes

Reaction equation

HRID 1175789 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[C:9]([O:16][CH3:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1.CN(C)C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH:13]([O:12][C:10]1[C:9]([O:16][CH3:17])=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:1][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[CH:11]=1)([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 312444-Methoxybenzaldehyde2×HCID 5049666Sodium triacetoxyborohydride2×HCID 12016998methyl 2-amino-4-isopropoxy-5-methoxybenzoate

Product 1

HCID 23153963HCID 23153963, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of methyl 2-amino-4-isopropoxy-5-methoxybenzoate (12.67 g), 4-methoxybenzaldehyde (7.90 g), N,N-dimethylformamide (150 ml) and acetic acid (3 ml) was stirred for 8 hours. After stirring, the sodium triacetoxyborohydride (13.4 g) was added thereto. The reaction mixture was stirred for 1 night. To the reaction mixture was added 4-methoxybenzaldehyde (1.98 g) and sodium triacetoxyborohydride (3.35 g) and stirred for 1 day. The reaction mixture was concentrated under reduced pressure until the amount was concentrated to a half, adjusted to pH 8˜9 by adding 5% sodium carbonate. Water was added thereto, the precipitated solid was collected by filtration, washed with water and dried to obtain the target compound (18.9 g).

Workup

  1. stirringAfter stirring
  2. stirringThe reaction mixture was stirred for 1 night
  3. stirringstirred for 1 day
  4. concentrationThe reaction mixture was concentrated under reduced pressure until the amount
  5. concentrationwas concentrated to a half
  6. additionby adding 5% sodium carbonate
  7. additionWater was added
  8. filtrationthe precipitated solid was collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-87c8a739e70b46b8b8f63476d6b171f5
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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