Acetone → HCID 11679981, compound

HRID 433014Notes

Reaction equation

HRID 433014 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH2:11])[C:5]([OH:7])=[O:6].CN(C)C=O.[CH3:17][C:18]([CH3:20])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(O)(=O)C>[NH2:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[NH:1][CH:18]([CH3:20])[CH3:17]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6228DimethylformamideHCID 692633,4-Diaminobenzoic acidHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 11679981HCID 11679981, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 3,4-diaminobenzoic acid (15.2 g), in 200 mL of tetrahydrofuran, 30 mL of dimethyl formamide, 7.3 mL of acetone, and 5.7 mL of acetic acid, was added 31.8 9 of sodium triacetoxyborohydride in portions. After 3 hours the mixture was filtered through diatomaceous earth and washed with tetrahydrofuran. The filtrate was concentrated to dryness. Crystallization of the residue with ethyl acetate/hexanes gave 11 grams of 4-amino-3-isopropylamino-benzoic acid.

Workup

  1. filtrationAfter 3 hours the mixture was filtered through diatomaceous earth
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate was concentrated to dryness
  4. customCrystallization of the residue with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9dd119bc382c4c339500bf38bb23636a
Source dataset
uspto-grants-2003_12
Patent number
US06664395B2

Reaction notes

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