4-Chloro-3,5-dinitrobenzoic acid → HCID 86593703, compound

HRID 1744709Notes

Reaction equation

HRID 1744709 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.[NH2:35][C@H:36]([CH3:48])[C:37]([NH:39][C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[CH:41]=1)=[O:38]>ClCCl>[CH3:46][C:44]1[CH:45]=[C:40]([NH:39][C:37](=[O:38])[C@H:36]([NH:35][C:6]([C:5]2[CH:4]=[C:3]([N+:14]([O-:16])=[O:15])[C:2]([Cl:1])=[C:10]([N+:11]([O-:13])=[O:12])[CH:9]=2)=[O:8])[CH3:48])[CH:41]=[C:42]([CH3:47])[CH:43]=1

Participants

5

Reactant 3

HCID 83774-Chloro-3,5-dinitrobenzoic acidHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 28213684HCID 28213684, compound

Product 1

HCID 86593703HCID 86593703, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of 4-chloro-3,5-dinitrobenzoic acid (1.058 g, 4.29 mmol) and EEDQ (1.062 g, 4.29 mmol) in dichloromethane (25 ml) is added (2R)-2-amino-N-(3,5-dimethylphenyl)propanamide, prepared in Example 5 (0.825 g, 4.29 mmol) in dichloromethane (25 ml). After 16 h of mixing at room temperature the product is recovered on a G-4 filter and washed with dichloromethane (30 ml). The product is dried at 50° C. for 4 h. 1.026 g (56%) of yellowish powder are obtained, mp 202°–204° C.

Workup

  1. additionAfter 16 h of mixing at room temperature the product
  2. customis recovered on a G-4
  3. filtrationfilter
  4. washwashed with dichloromethane (30 ml)
  5. customThe product is dried at 50° C. for 4 h
  6. custom1.026 g (56%) of yellowish powder are obtained

Sources & evidence

ORD record
ord-ade23b3a30804978aac13c98e32b157a
Source dataset
uspto-grants-2006_03
Patent number
US07018537B2

Reaction notes

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